Sodium borohydride → N-(4-(2-ethyl-1-hydroxybutyl)phenyl)acetamide

HRID 538884Notes

Reaction equation

HRID 538884 reaction equation
[CH2:1]([CH:3]([CH2:16][CH3:17])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[BH4-].[Na+]>CO>[CH2:16]([CH:3]([CH2:1][CH3:2])[CH:4]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=1)[OH:5])[CH3:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 43160160N-(4-(2-ethylbutanoyl)phenyl)acetamide

Product 1

HCID 22603035N-(4-(2-ethyl-1-hydroxybutyl)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(4-(2-ethylbutanoyl)phenyl)acetamide (730 mg, 3.13 mmol) in MeOH (20 mL) was cooled in an ice bath under N2 and treated with NaBH4 (148 mg, 3.91 mmol), added in one portion. The reaction vessel was removed from the ice bath and stirred overnight at RT. The reaction was concentrated and partitioned between DCM and half-saturated NaHCO3. The aqueous phase was extracted four times with DCM and the organic extracts were combined and dried over MgSO4, filtered and then concentrated. The crude product was purified by preparative TLC using 50% ethyl acetate in hexane as eluent to afford N-(4-(2-ethyl-1-hydroxybutyl)phenyl)acetamide as white solid. MS (ES+): m/z 236.24 (MH+).

Workup

  1. additionadded in one portion
  2. customThe reaction vessel was removed from the ice bath
  3. concentrationThe reaction was concentrated
  4. custompartitioned between DCM and half-saturated NaHCO3
  5. extractionThe aqueous phase was extracted four times with DCM
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by preparative TLC

Sources & evidence

ORD record
ord-d8d35d4e6124487885e43bfbbfc4d830
Source dataset
uspto-grants-2014_10
Patent number
US08865752B2

Reaction notes

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