1-(4-isopropoxyphenyl)propan-2-one → HCID 20227985, compound

HRID 1731575Notes

Reaction equation

HRID 1731575 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=O)[CH3:13])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[OH:15][CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)[CH2:17][NH2:18].[BH4-].[Na+]>CCCCCC>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:18][CH2:17][CH:16]([OH:15])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH3:13])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9193321-(4-isopropoxyphenyl)propan-2-oneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 4311764Sodium borohydride

Product 1

HCID 20227985HCID 20227985, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1-(4-Isopropoxyphenyl)propan-2-one (1.92 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (1.71 g) were condensed and subsequently reduced with sodium borohydride (2.00 g) by an analogous procedure to that described in Example 1. Chromatography of the crude product on silica gel using 1% methanol-dichloromethane as eluent gave N-[2-(4-isopropoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine, mp 58°-61° C. (hexane) as a 42:58 mixture of diastereoisomers.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-37a958ad7a114563b13d902f875dd658
Source dataset
uspto-grants-1986_11
Patent number
US04622342

Reaction notes

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