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

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-bb3f18366ce74ecf87b393633f01ba46
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091231B2

Linked notes

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