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

HRID 846696ノート

反応式

HRID 846696 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-dea24cc75284486b82b8dfcd210c9c85
出典データセット
uspto-grants-1992_08
特許番号
US05137892

反応ノート

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