Sodium borohydride → 1-Benzyl-4-methylpyrrolidin-3-ol

HRID 846696노트

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HRID 846696 반응식
[CH2:1]([N:8]1[CH2:12][CH:11]([CH3:13])[C:10](=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH2:1]([N:8]1[CH2:12][CH:11]([CH3:13])[CH:10]([OH:14])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 124309801-Benzyl-4-methylpyrrolidin-3-one

생성물 1

HCID 159347591-Benzyl-4-methylpyrrolidin-3-ol

시약·촉매·용매 1

HCID 702Ethanol용매2회

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온도
0 °C

실험 절차

A 15.58 g (82.3 mmol) sample of the ketone from step d was reduced to the alcohol by dissolving it in 32 mL of ethanol and adding the solution dropwise to a stirred suspension of sodium borohydride (3.11 g, 82.3 mmol) in 32 mL of ethanol at 0° C. The suspension was then stirred for 30 min at 0° C. and for 4 hours at room temperature. The solvent was then removed and the residue suspended in water. The product was extracted with methylene chloride and dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under vacuum. The crude product was purified in a kugelrohr apparatus (160°-180° C. @ 1.0 Torr) to yield 1-benzyl-4-methyl-3-pyrrolidinol, MS M/Z 192 (M+H); NMR (CDCl3) d 1.04 (d, 3H, J=7.5 Hz), 1.90 (dd, 1H, J=7.5 Hz, J=9.0 Hz), 2.14 (m, 1H), 2.55 (dd, 1H, J=6.0 Hz, J=10.5 Hz), 2.82 (dd, 1H, J=3.0 Hz, J=10.5 Hz), 3.13 (dd, 1H, J=3.0 Hz, J=3.0 Hz), 3.82 (m, 2H), 3.95 (m, 1H), 7.33 (m, 5H).

후처리

  1. additionadding the solution
  2. customThe solvent was then removed
  3. extractionThe product was extracted with methylene chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation under vacuum
  6. customThe crude product was purified in a kugelrohr apparatus (160°-180° C. @ 1.0 Torr)

출처 및 근거

ORD 기록
ord-dea24cc75284486b82b8dfcd210c9c85
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05137892

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