Water → HCID 67270991, compound

HRID 1697230Notes

Reaction equation

[F:1][C@@H:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:4]=[CH2:5].C([OH:24])(C)(C)C.C[N+]1([O-])CCOCC1.S([O-])([O-])=O.[Na+].[Na+].[OH2:39]>[Os]>[F:1][C@H:2]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:4]([OH:24])[CH2:5][OH:39]

Participants

Conditions

Temperature: 23 °C

Procedure

To a 250 mL RBF containing tert-butyl (1S,2R)-1-fluoro-1-phenylbut-3-en-2-ylcarbamate (105.00 mg, 396 μmol)(mixture of diasteromers at benzylic fluoride stereocenter) was added tert-butanol (3 mL) and water (1 ml). The mixture was allowed to stir at 23° C. for 2 min, then NMO (139 mg, 1187 μmol) and osmium tetraxide (124 μl, 396 μmol) were added and the reaction was allowed to stir for another 48 h. before the reaction was quenched with water and sodium sulfite (1496 mg, 11872 μmol). The reaction was allowed to stir for 15 min and then extracted with EtOAc (3×). The combined organics were washed with HCl (1 N), sodium bicarbonate, brine and dried over sodium sulfate. The dried solution was passed through a plug of silica gel and concentrated to give 102 mg of a colorless oil

Workup

stirringto stir for another 48 h. before the reaction
stirringto stir for 15 min
extractionextracted with EtOAc (3×)
washThe combined organics were washed with HCl (1 N), sodium bicarbonate, brine
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-3288873dcc4047e99da710c31337cf04
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163909B2

Reaction notes

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