Methyl morpholine oxide → (Z)-7-[(1R,2S,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-chloro-2-(4-formyl-phenyl)-cyclopentyl]-hept-5-enoic acid methyl ester

HRID 9238

반응식

HRID 9238 반응식
[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]1[C@H:14]([Cl:15])[CH2:13][C@@H:12]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C@@H:11]1[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][CH:25]=1.C[N+]1([O-])CCOCC1>ClCCl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:1][O:2][C:3](=[O:32])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@H:10]1[C@H:14]([Cl:15])[CH2:13][C@@H:12]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C@@H:11]1[C:24]1[CH:29]=[CH:28][C:27]([CH:30]=[O:31])=[CH:26][CH:25]=1

참가 물질

5

반응물 2

HCID 82029Methyl morpholine oxideHCID 69595650(Z)-7-[(1R,2S,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-chloro-2-(4-hydroxymethyl-phenyl)-cyclopentyl]-hept-5-enoic acid methyl ester

생성물 1

HCID 59794679(Z)-7-[(1R,2S,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-chloro-2-(4-formyl-phenyl)-cyclopentyl]-hept-5-enoic acid methyl ester수율 79.7%

시약·촉매·용매 2

HCID 178419074HCID 178419074, 화합물촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

An ice cold mixture of 9-1 (43 mg, 0.089 mmol), 4 Å molecular sieves (56 mg) and NMO (16 mg, 0.14 mmol) in dichloromethane (0.5 mL) was treated with TPAP (3 mg, 0.009 mmol). The mixture was stirred for 5 min. at 0° C. and then for 1 h at room temperature. The mixture was then filtered through a pad of silica gel, washing with ethyl acetate. The solvents were evaporated and the residue was purified by flash chromatography on silica gel (10% ethyl acetate/hexanes) to give 9-2 (34 mg, 79%).

후처리

  1. waitfor 1 h at room temperature
  2. filtrationThe mixture was then filtered through a pad of silica gel
  3. washwashing with ethyl acetate
  4. customThe solvents were evaporated
  5. customthe residue was purified by flash chromatography on silica gel (10% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-bb3f18366ce74ecf87b393633f01ba46
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091231B2

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