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

HRID 1785032Notes

Reaction equation

HRID 1785032 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:13]C(=O)OC(C)(C)C)[CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.[ClH:21].O1CCOCC1>>[ClH:21].[NH2:13][C@@H:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH2:10][CH2:11][OH:12]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 575943931,1-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-35fbad4d62654a16af7fbd074cf502cf
Source dataset
uspto-grants-2009_03
Patent number
US07504413B2

Reaction notes

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