1,4-Dioxane hydrochloride → (3S)-3-Amino-4-(4-bromophenyl)-1-butanol hydrochloride

HRID 730330Notes

Reaction equation

HRID 730330 reaction equation
CC([N:5]([C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)[CH2:10][CH2:11][OH:12])C(=O)[O-])(C)C.[ClH:21].O1CCOCC1>>[ClH:21].[NH2:5][C@@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([Br:20])=[CH:18][CH:19]=1)[CH2:10][CH2:11][OH:12]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 866400931,1-Dimethylethyl{(1S)-1-[(4-bromophenyl)methyl]-3-hydroxypropyl}carbamate

Product 1

HCID 67277825(3S)-3-Amino-4-(4-bromophenyl)-1-butanol hydrochlorideYield 94%

Procedure

1,1-Dimethylethyl{(1S)-1-[(4-bromophenyl)methyl]-3-hydroxypropyl}carbamate (4.4 g, 12.8 mmol) was dissolved in 4N HCl/dioxane (20 mL). After 2 h, the reaction mixture was concentrated in vacuo to give 3.69 g (94%) of the title compound as a white solid. LC/MS (ES) m/e 244.0 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-6fec0ffd755e43419d5e12b8cc4ecf7b
Source dataset
uspto-grants-2009_09
Patent number
US07582668B2

Reaction notes

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