Ammonia methanol → HCID 86639449, compound

HRID 451814

Reaction equation

HRID 451814 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:12][N@@:11]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:20].CO>>[NH2:20][CH2:12][C@H:10]([NH:11][C:13](=[O:14])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 72525716(S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate

Product 1

HCID 86639449HCID 86639449, compoundYield 47%

Procedure

A solution of (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)aziridine-1-carboxylate (5 g, 17.42 mmol) in NH3/MeOH (50 mL) was stirred at 50-60° C. for 48 h. After the reaction was complete, the mixture was concentrated in vacuo. The residue was purified on silica gel chromatography to afford (S)-tert-butyl 1-amino-3-(tert-butyldimethylsilyloxy)propan-2-ylcarbamate (2.5 g, 47%). 1H NMR (CDCl3, 300 MHz) δ 3.67 (m, 3H), 2.88 (d, 2H), 2.71 (s, 3H), 1.44 (s, 9H), 0.88 (s, 9H), 0.0 (s, 6H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified on silica gel chromatography

Sources & evidence

ORD record
ord-0f03dc6efce74bebb63c9946a11f9d57
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Linked notes

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