Sodium borohydride → N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine

HRID 851173Notes

Reaction equation

HRID 851173 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([OH:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[CH3:15])=[CH:9][CH:8]=1)(OC)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([OH:29])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:28])[F:26])[CH:20]=2)[CH3:15])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19874581N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-trifluoromethylphenyl) ethanamine

Product 1

HCID 13079625N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamineYield 86.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[2-(4-carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine (1.0 g) in absolute methanol (50 ml) at ambient temperature was added sodium borohydride (1.0 g) in small portions over a period of 30 minutes with vigorous stirring. The mixture was boiled under reflux for 2 hours, cooled to room temperature and the solvent removed under vacuum. The residue was partitioned between water and dichloromethane, the organic layer dried (MgSO4) and evaporated to yield a brown oil (0.81 g) which on chromatography on silica-gel in dichloromethane/methanol mixtures gave a waxy solid. Recrystallisation from 50% 40.60 petroleum ether--ether gave a white solid (0.25 g) m.p. 91°-97° C., as a 58:42 mixture of diastereoisomers.

Workup

  1. temperatureunder reflux for 2 hours
  2. customthe solvent removed under vacuum
  3. customThe residue was partitioned between water and dichloromethane
  4. dry with materialthe organic layer dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-2bc507e7e47044209e1aa1c24630a5b9
Source dataset
uspto-grants-1983_05
Patent number
US04382958

Reaction notes

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