Ammonium Hydroxide → HCID 59593777, compound

HRID 2261907Notes

Reaction equation

HRID 2261907 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@:8]([CH3:19])([CH: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].[NH4+:21].[OH-]>CCO>[NH2:21][CH2:18][CH:16]([OH:17])[C@:8]([NH:7][C:6](=[O:20])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:19]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 91243547HCID 91243547, compound

Product 1

HCID 59593777HCID 59593777, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl((1R)-1-methyl-1-oxiran-2-yl-2-phenylethyl)carbamate (986 mg, 3.56 mmol) in EtOH (35 mL) and NH4OH (35 mL) was stirred at 60° C., sealed, for 16 h, concentrated in vacuo and purified by flash chromatography (silica, 0-30% (10% NH4OH/MeOH)/CH2Cl2) to provide tert-butyl ((1R)-3-amino-1-benzyl-2-hydroxy-1-methylpropyl)carbamate as a thick oil. 1H NMR (400 MHz, CD3OD, 1:1 diastereomeric mixture) δ 7.30-7.14 (m, 5H), 4.01 (br d, J=9.2 Hz, 0.5H), 3.54 (dd, J=10.0, 2 Hz, 0.5H), 3.39 (br s, 0.5H), 3.36 (br s, 0.5H), 2.94-2.56 (m, 4H), 1.47 (s, 9H), 1.03 (s, 1.5H), 0.99 (s, 1.5H).

Workup

  1. customsealed, for 16 h
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography (silica, 0-30% (10% NH4OH/MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-869bdae634ba4744bbcfa55cce1dc21d
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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