Sodium Carbonate → HCID 66704854、化合物

HRID 424738ノート

反応式

HRID 424738 の反応式
[CH2:1]([N:8]1[CH2:12][C@H:11]([CH3:13])[C@@H:10]([C:14]([NH:16][CH:17]2[CH2:19][CH2:18]2)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][C@H:11]([CH3:13])[C@@H:10]([CH2:14][NH:16][CH:17]2[CH2:19][CH2:18]2)[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 10340Sodium CarbonateHCID 45087015HCID 45087015、化合物

生成物 1

HCID 66704854HCID 66704854、化合物収率 93.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

(3R,4R)-1-Benzyl-N-cyclopropyl-4-methyl-3-pyrrolidinecarboxamide (70.0 g) was dissolved in toluene (700 mL). While this solution was chilled in an ice water bath, a borane/dimethyl sulfate complex (90%, 34.3 mL) was added dropwise. The mixture was then stirred for 15 min, was refluxed and was allowed to cool to room temperature. A 10% aqueous Na2CO3 solution (400 mL) was added, and the mixture was stirred at 100° C. for 2 hours and was then allowed to cool to room temperature. The toluene layer was separated, washed with water (2×250 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by distillation under reduced-pressure to give (3S,4R)-1-benzyl-3-cyclopropylaminomethyl-4-methylpyrrolidine as a colorless oil (62.1 g).

後処理

  1. temperatureWhile this solution was chilled in an ice water bath
  2. additiona borane/dimethyl sulfate complex (90%, 34.3 mL) was added dropwise
  3. temperaturewas refluxed
  4. stirringthe mixture was stirred at 100° C. for 2 hours
  5. temperatureto cool to room temperature
  6. customThe toluene layer was separated
  7. washwashed with water (2×250 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. distillationThe resulting residue was purified by distillation under reduced-pressure

出典と根拠

ORDレコード
ord-08833b8c444b458da28662245dff9d72
出典データセット
uspto-grants-2012_01
特許番号
US08106072B2

反応ノート

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