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

HRID 1894749노트

반응식

HRID 1894749 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-1f03080f36834e0483215740a641c965
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513291B2

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