| Identification | Back Directory | [Name]
N-(TERT-BUTOXYCARBONYL)-D-PROLINAL | [CAS]
73365-02-3 | [Synonyms]
BOC-D-PROLINAL
(R)-N-BOC-PROLINAL
N-T-BOC-D-PROLINAL
(R)-N-BOC-PROLINAL, 97+%
(R)-1-Boc-2-formylpyrrolidine
N-(TERT-BUTOXYCARBONYL)-D-PROLINAL
(R)-(+)-1-BOC-2-PYRROLIDINECARBALDEHYDE
S-(+)-N-(diphenylmethylene)glycinesultam
(R)-tert-butyl 2-forMylpyrrolidine-1-carboxylate
tert-butyl (2R)-2-formylpyrrolidine-1-carboxylate
(R)-2-FORMYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
1-Pyrrolidinecarboxylicacid, 2-formyl-, 1,1-dimethylethyl ester, (2R)-
(R)-2-FORMYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER (R)-N-BOC-PROLINAL | [EINECS(EC#)]
624-637-4 | [Molecular Formula]
C10H17NO3 | [MDL Number]
MFCD01321389 | [MOL File]
73365-02-3.mol | [Molecular Weight]
199.25 |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless to yellow liquid | [alpha ]
+83°(23℃, neat) | [Boiling point ]
228 °C(lit.)
| [density ]
1.059 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.461(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Freezer (-20°C) | [form ]
Liquid | [pka]
-3.03±0.40(Predicted) | [color ]
Colorless to yellow | [Specific Gravity]
1.059 | [Optical Rotation]
[α]23/D +83°, neat | [Sensitive ]
Air Sensitive | [InChI]
InChI=1S/C10H17NO3/c1-10(2,3)14-9(13)11-6-4-5-8(11)7-12/h7-8H,4-6H2,1-3H3/t8-/m1/s1 | [InChIKey]
YDBPZCVWPFMBDH-MRVPVSSYSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CCC[C@@H]1C=O |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless to yellow liquid | [Uses]
peptide synthesis | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
1. tert-Butyl (2R)-2-formylpyrrolidine-1-carboxylate (15.9 g, 37.4 mmol) was added in batches to a stirring solution of tert-Butyl (2R)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (5.0 g, 24.9 mmol) in dichloromethane (75 mL) under nitrogen protection over a 5-minute dosing period. 2. The reaction mixture was stirred for 1 hr. to form a suspension.3. The suspension was filtered through a diatomaceous earth pad and the filter cake was washed with dichloromethane (100 mL).4. The filtrate was concentrated under pressure to give the crude product.5. The crude product was purified by neutral silica gel column chromatography to give BOC-D-prolinyl aldehyde (4.4 g, 89% yield) using 12% ethyl acetate/hexanes as eluent. | [References]
[1] Patent: WO2015/120390, 2015, A1. Location in patent: Page/Page column 97; 178
[2] Tetrahedron Letters, 1997, vol. 38, # 37, p. 6479 - 6482
[3] Patent: WO2015/118342, 2015, A1. Location in patent: Page/Page column 94; 95
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 12, p. 3190 - 3198
[5] Tetrahedron Letters, 1990, vol. 31, # 28, p. 3957 - 3960 |
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