Dimethyl Sulfide → 4-Amino-2-phenylbutan-2-ol

HRID 2037398Notes

Reaction equation

HRID 2037398 reaction equation
[OH:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[CH2:3][C:4]#[N:5].S(C)C>C1COCC1>[NH2:5][CH2:4][CH2:3][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([OH:1])[CH3:6]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 5392333-Hydroxy-3-phenylbutanenitrile

Product 1

HCID 249751014-Amino-2-phenylbutan-2-olYield 117.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxy-3-phenylbutanenitrile (1 g, 6.2 mmol) in THF (10 mL) was added dropwise BH3.Me2S (32 mL, 62 mmol) under a N2 atmosphere. The mixture was stirred at rt overnight. The reaction was quenched with MeOH (10 mL). The mixture was concentrated to give crude 4-amino-2-phenylbutan-2-ol (1.2 g, crude), which was used in the next step without further purification.

Workup

  1. customThe reaction was quenched with MeOH (10 mL)
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-644c52a018d04052a0e06485f4f0fdc6
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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