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

HRID 1894749Notes

Reaction equation

HRID 1894749 reaction equation
[CH3:1][N:2]([CH3:18])[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].[BH4-].[Na+]>CO>[CH3:18][N:2]([CH3:1])[CH:3]([CH2:16][CH3:17])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)[OH:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86681892N-(4-(2-(dimethylamino)butanoyl)phenyl)acetamide

Product 1

HCID 86681893N-(4-(2-(dimethylamino)-1-hydroxybutyl)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(4-(2-(dimethylamino)butanoyl)phenyl)acetamide (3.80 g, 15.30 mmol) in 40 mL MeOH was cooled in an ice bath under N2 and treated with NaBH4 (725 mg, 19.12 mmol), added in one portion. The reaction vessel was removed from the ice bath and stirred at rt over the weekend. The reaction was quenched with acetone, then concentrated in vacuo 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 Na2SO4. The solution was decanted and concentrated in vacuo. The solid residue was purified by silica gel column chromatography eluting with 10%-12% MeOH (2N NH3)/DCM to provide the syn-isomer of N-(4-(2-(dimethylamino)-1-hydroxybutyl)phenyl)acetamide as a white amorphous solid and the anti-isomer as a straw colored oil. MS ESI: m/z 251.17 [M+1+].

Workup

  1. additionadded in one portion
  2. customThe reaction vessel was removed from the ice bath
  3. customThe reaction was quenched with acetone
  4. concentrationconcentrated in vacuo
  5. custompartitioned between DCM and half-saturated NaHCO3
  6. extractionThe aqueous phase was extracted four times with DCM
  7. dry with materialdried over Na2SO4
  8. customThe solution was decanted
  9. concentrationconcentrated in vacuo
  10. customThe solid residue was purified by silica gel column chromatography
  11. washeluting with 10%-12% MeOH (2N NH3)/DCM

Sources & evidence

ORD record
ord-1f03080f36834e0483215740a641c965
Source dataset
uspto-grants-2013_08
Patent number
US08513291B2

Reaction notes

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