(3R*,4R*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamide → (3R*,4S*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamide

HRID 862118노트

반응식

HRID 862118 반응식
[CH2:1]([N:3]([CH2:31][CH3:32])[C:4]([C@@H:6]1[C@H:11]2[CH2:12][CH2:13][N:8]([CH:9]([CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:10]32[O:17][CH2:16][CH2:15][O:14]3)[CH2:7]1)=[O:5])[CH3:2]>C[O-].[Na+]>[CH2:31]([N:3]([CH2:1][CH3:2])[C:4]([C@@H:6]1[C@@H:11]2[CH2:12][CH2:13][N:8]([CH:9]([CH:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:10]32[O:17][CH2:16][CH2:15][O:14]3)[CH2:7]1)=[O:5])[CH3:32]

참가 물질

3

반응물 1

HCID 53633469(3R*,4R*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamide

생성물 1

HCID 53633467(3R*,4S*)-N,N-Diethyl-6-diphenylmethyl-5,5-ethylenedioxy-1-azabicyclo[2.2.2]octane-3-carboxamide수율 87%

시약·촉매·용매 1

HCID 10942334Sodium Methoxide용매

실험 절차

A suspension of 21 (9.8 g, 22 mmol) in sodium methoxide (28% in MeOH; 400 g) was heated at reflux temperature for 9 hours. The resulting solution was poured on ice (300 ml) and extracted with CH2Cl2 (150 ml) three times. The combined extracts were dried over sodium sulfate (Na2SO4) and concentrated. The clude was purified by recrystallization from ethanol (EtOH) to give 22 (1:4 mixture at 6-position; 8.4 g, 19 mmol, 87%).

후처리

  1. temperaturewas heated
  2. temperatureat reflux temperature for 9 hours
  3. additionThe resulting solution was poured on ice (300 ml)
  4. extractionextracted with CH2Cl2 (150 ml) three times
  5. dry with materialThe combined extracts were dried over sodium sulfate (Na2SO4)
  6. concentrationconcentrated
  7. customThe clude was purified by recrystallization from ethanol (EtOH)

출처 및 근거

ORD 기록
ord-6f9986fb4c534a89a3371528cd179af1
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05716965

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