Ammonia → tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamate

HRID 852571Notes

Reaction equation

HRID 852571 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]([C@H:16]1[CH2:18][O:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[NH3:20]>CO>[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C@H:16]([OH:17])[CH2:18][NH2:20])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 9903372(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane

Product 1

HCID 10333883tert-butyl (2S,3R)-4-amino-3-hydroxy-1-phenylbutan-2-ylcarbamateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ((S)-(S)-1-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester (D101) (25 g, 95.1 mmol, 1 equiv)) in MeOH (350 ml) was added aqueous ammonia (32% w/w, 180 ml, 3.2 mol, 3.3 equiv). The resulting mixture was stirred at room temperature for 16 h then concentrated in vacuo to give ((1S,2R)-3-amino-1-benzyl-2-hydroxy-propyl)-carbamic acid tert-butyl ester (D102) (25.2 g, 95%) as a white solid.

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-747700bcd7324620b791a82982aa2cf2
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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