Sodium borohydride → tert-Butyl [1-(4-fluorophenyl)-2-hydroxy-2-naphthalen-1-ylethyl]carbamate

HRID 1170398Notes

Reaction equation

HRID 1170398 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1.P([O-])(O)(O)=O.[Na+]>CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH:11]([OH:12])[C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 23672064Monosodium phosphateHCID 86621956Tert-butyl [1-(4-fluorophenyl)-2-naphthalen-1-yl-2-oxoethyl]carbamate

Product 1

HCID 86621955tert-Butyl [1-(4-fluorophenyl)-2-hydroxy-2-naphthalen-1-ylethyl]carbamateYield 102.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

0.72 g (18.9 mmol) of sodium borohydride was added in 4 portions to a solution of 7.2 g (18.9 mmol) of tert-butyl [1-(4-fluorophenyl)-2-naphthalen-1-yl-2-oxoethyl]carbamate in 75 ml of methanol at 0-5° C. The reaction mixture was stirred at 0-5° C. for 1 h and then poured into an aqueous sodium dihydrogen phosphate solution (80 g/l). Extraction twice with ethyl acetate was followed by drying on magnesium sulfate. Concentration resulted in 7.4 g of tert-butyl [1-(4-fluorophenyl)-2-hydroxy-2-naphthalen-1-ylethyl]carbamate (diastereoisomer mixture: 85/15) as a pale yellow oil (yield: quantitative). The substance was used without further purification for the next stage.

Workup

  1. extractionExtraction twice with ethyl acetate
  2. customby drying on magnesium sulfate
  3. concentrationConcentration

Sources & evidence

ORD record
ord-52e06d22dd3d426095beef3474a8f9b3
Source dataset
uspto-grants-2010_11
Patent number
US07825264B2

Reaction notes

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