| Identification | Back Directory | [Name]
N-Methyl-D-prolinol | [CAS]
99494-01-6 | [Synonyms]
-D-proL
N-METHYL-D-PROLINOL
1-Methyl-D-prolinol
N-Methyl-D-Prolinol,>98%
N-Methyl-D-prolinol USP/EP/BP
(R)-N-methylpyrrolidine-2-methanol
(R)-1-METHYL-2-PYRROLIDINEMETHANOL
(?-1-Methylpyrrolidin-2-yl)methanol
((R)-1-methylpyrrolidin-2-yl)methanol
[(2R)-1-methyl-2-pyrrolidinyl]methanol
[(2R)-1-Methylpyrrolidin-2-yl]Methanol
(R)-2-Hydroxymethyl-1-methylpyrrolidine
2-Pyrrolidinemethanol, 1-methyl-, (2R)-
(R)-(-)-(1-METHYL-2-PYRROLIDINYL)METHANOL | [Molecular Formula]
C6H13NO | [MDL Number]
MFCD07368622 | [MOL File]
99494-01-6.mol | [Molecular Weight]
115.17 |
| Chemical Properties | Back Directory | [density ]
0.971 g/mL at 25 °C | [refractive index ]
n20/D4.469 | [Fp ]
71℃ | [storage temp. ]
2-8°C | [form ]
liquid | [pka]
14.77±0.10(Predicted) | [Appearance]
Colorless to light yellow Liquid | [Optical Rotation]
Consistent with structure | [Boiling point ]
68-71°C(lit.) | [InChI]
InChI=1S/C6H13NO/c1-7-4-2-3-6(7)5-8/h6,8H,2-5H2,1H3/t6-/m1/s1 | [InChIKey]
VCOJPHPOVDIRJK-ZCFIWIBFSA-N | [SMILES]
N1(C)CCC[C@@H]1CO |
| Hazard Information | Back Directory | [Uses]
N-Methyl-D-prolinol is used as a pharmaceutical or synthetic intermediate component in the preparation of organic compounds such as nitrogen-containing heterocyclic compounds, pyrotinib intermediate and anidulafungin derivative. | [Synthesis]
Step 1: Preparation of [(2R)-1-methylpyrrolidin-2-yl]methanol
Lithium aluminum hydride (230 mg, 6 mmol) and N-tert-butoxycarbonyl-R-prolinol (400 mg, 2 mmol) were dissolved in 10 mL of dry tetrahydrofuran and cooled in an ice water bath. After no significant gas release, the reaction mixture was heated to reflux and maintained for 2 hours. Upon completion of the reaction, the mixture was slowly added dropwise to 5 mL of methanol in an ice-water bath, followed by the addition of 5 mL of water. The mixture was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford N-methyl-D-prolinol [(2R)-1-methylpyrrolidin-2-yl]methanol (221 mg, 77.0% yield) as a colorless oil. Mass spectrum (ESI) m/z: 116 [M + 1]. | [References]
[1] Patent: US2013/338190, 2013, A1. Location in patent: Paragraph 0037; 0038
[2] Patent: EP2684877, 2014, A2. Location in patent: Page/Page column 0032; 0033
[3] Patent: TWI524893, 2016, B. Location in patent: Page/Page column 44; 45
[4] Patent: WO2018/31877, 2018, A1. Location in patent: Paragraph 00150 |
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