Water → (S)-b-Amino-3,4-dimethoxybenzenepropanol

HRID 1739431Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)[NH2:11].O.[OH-].[Na+]>O1CCCC1>[NH2:11][C@@H:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)[CH2:9][OH:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of lithium aluminum hydride (7.75 g) in tetrahydrofuran (200 ml) is gradually added dropwise a solution of 3-(3,4-dimethoxyphenyl)-L-alanine methyl ester (12.2 g) in tetrahydrofuran (100 ml) at 0° C. The reaction mixture is stirred at 0° C. for 30 minutes, and then thereto are added dropwise water (7.7 ml), 10% aqueous sodium hydroxide solution (7.7 ml) and water (23.1 ml). The reaction mixture is stirred at room temperature overnight, and filtered through a cerite pad. The filtrate is concentrated to give (2S)-2-amino-3-(3,4-dimethoxyphenyl)-1-propanol (10.8 g) as an brown oily product.

Workup

stirringThe reaction mixture is stirred at room temperature overnight
filtrationfiltered through a cerite pad
concentrationThe filtrate is concentrated

Sources & evidence

ORD record: ord-9c73f0c635ea4f15b398e531a90a3898
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05965730

Reaction notes

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