1-Phenyl-2-pyrrolidin-1-ylethanol → HCID 7195215、化合物

HRID 1715867ノート

反応式

HRID 1715867 の反応式
C(OC(=O)[C@@H]([C@H](C(OC(=O)C1C=CC=CC=1)=O)O)O)(=O)C1C=CC=CC=1.[C:27]1([CH:33]([OH:40])[CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CO.[OH-].[Na+]>[C:27]1([C@@H:33]([OH:40])[CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

5

反応物 2

HCID 2212131-Phenyl-2-pyrrolidin-1-ylethanolHCID 12858288di-O-benzoyl-L-tartaric acid

生成物 1

HCID 7195215HCID 7195215、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒3 回HCID 14798Sodium Hydroxide溶媒

実験手順

Solutions of 35.8 g of di-O-benzoyl-L-tartaric acid in 150 ml methanol and 19.1 g of 1-phenyl-2-(1-pyrrolidinyl)-ethanol in 100 ml of methanol were mixed and the mixture left standing in a refrigerator for 2 days. The crystalline product was filtered off, washed with a small amount of cold methanol and diethyl ether and dried. The product was repeatedly recrystallised from hot ethanol, yielding an optically pure diastereomeric salt of 15.0 g. The free base was released by dissolving the salt in 100 ml of cold 20% aqueous sodium hydroxide and extracted in dichloromethane. After evaporation of the solvent, 7.2 g (38% based on the starting racemate) of the oily (R)-enantiomer of 1-phenyl-2-(1-pyrrolidinyl)-ethanol were obtained which solidified after storage in a refrigerator to become a crystalline mass. The product had a [αD20] value of −40° (methanol).

後処理

  1. waitthe mixture left
  2. filtrationThe crystalline product was filtered off
  3. washwashed with a small amount of cold methanol and diethyl ether
  4. customdried
  5. customThe product was repeatedly recrystallised from hot ethanol
  6. customyielding an optically pure diastereomeric salt of 15.0 g
  7. extractionextracted in dichloromethane
  8. customAfter evaporation of the solvent, 7.2 g (38%
  9. customwere obtained which

出典と根拠

ORDレコード
ord-17990049b1de442283f5c14201e7355e
出典データセット
uspto-grants-2010_09
特許番号
US07799952B2

反応ノート

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