Water → N-[2-(4-(3-Carbomethoxyprop-2-eneoxy)phenyl)-1-methylethyl]-2-hydroxy-2-(4-chlorophenyl) ethanamine

HRID 1758978Notes

Reaction equation

[C:1]([CH:5]=[CH:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](=O)[CH3:17])=[CH:11][CH:10]=1)([O:3][CH3:4])=[O:2].[OH:19][CH:20]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[CH2:21][NH2:22].O>C1C=CC=CC=1>[C:1]([CH:5]=[CH:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:22][CH2:21][CH:20]([OH:19])[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH3:17])=[CH:11][CH:10]=1)([O:3][CH3:4])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1-(4-(3-carbomethoxyprop-2-eneoxy) phenyl) propan-2-one (2.27 g) and 2-hydroxy-2-(4-chlorophenyl) ethanamine (1.57 g) in benzene (100 ml) was boiled under reflux with azeotropic removal of water using a Dean and Stark trap. The solution was evaporated, the residue dissolved in methanol (50 ml), cooled in ice and sodium borohydride added. The solution was stirred for 1 hour at 0° C., the methanol evaporated, and the residue partitioned between water and ethyl acetate. The ethyl acetate layer was dried (MgSO4) and evaporated to give a cream solid (3.1 g) which was crystallised from ethyl acetate m.p. 120°-122°. as a 0:100 mixture of diastereoisomers. Recrystallisation of the mother liquors from hexane gave a 70:30 mixture of diastereoisomers, m.p. 55°-65°.

Workup

customThe solution was evaporated
dissolutionthe residue dissolved in methanol (50 ml)
temperaturecooled in ice
additionsodium borohydride added
customthe methanol evaporated
customthe residue partitioned between water and ethyl acetate
dry with materialThe ethyl acetate layer was dried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-6fafafae0c994d71975a9d13a33527df
Source dataset: uspto-grants-1982_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04338333

Reaction notes

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