| Identification | More | [Name]
(S)-TERT-LEUCINOL | [CAS]
112245-13-3 | [Synonyms]
2-AMINO-3,3-DIMETHYL-1-BUTANOL
H-(TBU)GLY-OL
H-TLE-OL
L-T-BUTYLGLYCINOL
L-(+)-TERT-LEUCINOL
L-TERT-LEUCINOL
L-T-LEUCINOL
(S)-2-AMINO-3,3-DIMETHYL-1-BUTANOL
(S)-2-AMINO-3,3-DIMETHYLBUTANOL
(S)-TERT-LEUCINOL
(S)-TERT-LENCINOL
(S)-TERT-LEACINOL
(2S)-1-HYDROXY-3,3-DIMETHYL-BUTAN-2-YL]AZANIUM
(S)-2-Amino-3,3-dimethyl-1-butanol, L-tert-Leucinol
(+)-tert-Leucinol
(2S)-2-Amino-3,3-dimethyl-1-butanol
(S)-2-tert-Butyl-2-aminoethanol
(S)-3,3-Dimethyl-2-amino-1-butanol
(2R)-2-Amino-3,3-dimethyl-1-butanol
(R)-3,3-Dimethyl-2-aminobutane-1-ol | [Molecular Formula]
C6H15NO | [MDL Number]
MFCD00192250 | [Molecular Weight]
117.19 | [MOL File]
112245-13-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline low melting solid | [Melting point ]
30-34 °C(lit.)
| [Boiling point ]
114-116 °C (10 mmHg)
| [density ]
0.9 g/mL at 25 °C(lit.)
| [refractive index ]
38 ° (C=1.5, EtOH) | [Fp ]
194 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
soluble in Methanol | [form ]
Crystalline Low Melting Mass or Liquid | [pka]
12.88±0.10(Predicted) | [color ]
White or colorless | [Optical Rotation]
[α]26/D +37°, c = 1.5 in ethanol | [BRN ]
3600321 | [Major Application]
peptide synthesis | [InChI]
InChI=1S/C6H15NO/c1-6(2,3)5(7)4-8/h5,8H,4,7H2,1-3H3/t5-/m1/s1 | [InChIKey]
JBULSURVMXPBNA-RXMQYKEDSA-N | [SMILES]
C(O)[C@@H](N)C(C)(C)C | [CAS DataBase Reference]
112245-13-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10-23 | [HS Code ]
29221990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
L-tert-Leucine-->Lithium borohydride-->Methanol-->Tetrahydrofuran-->Chlorotrimethylsilane | [Preparation Products]
(R)-(+)-2-Methyl-2-propanesulfinamide-->Oxazole, 2,2'-(1-methylethylidene)bis[4,5-dihydro-4-methyl-, (4S,4'S)--->2,2'-Bioxazole, 4,4'-bis(1,1-dimethylethyl)-4,4',5,5'-tetrahydro-, (4S,4'S)--->(S,S)-(-)-2,2'-ISOPROPYLIDENEBIS(4-TERT-BUTYL-2-OXAZOLINE)-->Olorinab-->(4R)-4-T-BUTYL-2-METHYL 2-OXAZOLINE |
| Hazard Information | Back Directory | [Chemical Properties]
white crystalline low melting mass or | [Uses]
Useful amino acid employed in various asymmetric reactions. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
GENERAL STEPS: Example 8-1; To a 100 mL Schlenk tube purged with nitrogen was added 4.00 g (30.5 mmol) of (S)-tert-leucine and 40 mL of tetrahydrofuran, and the temperature of the reaction system was adjusted to 10°C. Over 5 min, 1.46 g (61.0 mmol) of lithium borohydride was added to the suspension in batches, followed by adjusting the temperature of the system to 20 °C. Over 30 minutes, 7.44 g (67.1 mmol) of trimethylmethylsilyl chloride was added slowly and dropwise, then the mixture was heated to 65 °C and stirred continuously at this temperature for 3 hours. Upon completion of the reaction, the mixture was cooled to 10 °C and quenched by the slow dropwise addition of 4 mL of methanol over 20 min. After concentrating the reaction mixture using a rotary evaporator, 40 mL of 4 M aqueous sodium hydroxide solution was added and stirred for 1 hour at room temperature. Subsequently, 40 mL of tert-butyl methyl ether was added for extraction and the organic layer was separated and dried with anhydrous sodium sulfate. After filtration to remove the desiccant, the tert-butyl methyl ether was removed by atmospheric pressure distillation. Finally, the 70 to 75 °C fraction was collected by reduced pressure distillation (0.3 kPa) to give 2.96 g of (S)-tert-leucinol in 83% yield. | [References]
[1] Journal of the American Chemical Society, 2003, vol. 125, # 21, p. 6362 - 6363
[2] Chemical Communications, 2010, vol. 46, # 3, p. 445 - 447
[3] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 1637 - 1642
[4] Journal of Organic Chemistry, 1992, vol. 57, # 17, p. 4732 - 4740
[5] Organic Letters, 2018, vol. 20, # 16, p. 4806 - 4810 |
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