Citric Acid → (S)-4-(3-Hydroxy-2-methyl-propyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one

HRID 479037

반응식

HRID 479037 반응식
C[O:2][C:3](=O)[CH:4]([CH3:20])[CH2:5][C@H:6]1[CH2:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH2:7]1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O>CCO>[OH:2][CH2:3][CH:4]([CH3:20])[CH2:5][C@@H:6]1[CH2:7][N:8]([C@H:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:13])[C:9](=[O:11])[CH2:10]1

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 590940382-Methyl-3-[(S)-5-oxo-1-((S)-1-phenyl-ethyl)-pyrrolidin-3-yl]-propionic Acid Methyl Ester

생성물 1

HCID 59093973(S)-4-(3-Hydroxy-2-methyl-propyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one수율 59%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

To the ester 93 (4.82 g, 0.017 mol) in EtOH (100 mL) was added NaBH4 (3.7 g, 0.10 mol) and the mixture heated to reflux for 2.5 hours. The solution was cooled to 0° C. and 1 M citric acid carefully added followed by water. The solution was concentrated to half volume added and extracted with ether. The combined organic extracts were dried (MgSO4) and concentrated. Flash chromatography (1:1 hexane/acetone) of the residue gave the product as an oil (2.6 g, 59%). MS m/z 262 (M+H, 100%).

후처리

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2.5 hours
  3. concentrationThe solution was concentrated to half volume
  4. additionadded
  5. extractionextracted with ether
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5f9e41891af7422cb0aaa7efa916ab43
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642398B2

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