Water → HCID 67270991, compound

HRID 1039702

Reaction equation

HRID 1039702 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

7

Reactant 5

HCID 962Water2×HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 86635707HCID 86635707, compound

Product 1

HCID 67270991HCID 67270991, compound

Reagents, catalysts & solvents 1

HCID 23937OsmiumCatalyst

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 mmol)(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 mmol) and osmium tetraxide (124 μA, 396 mmol) 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 mmol). 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

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

Sources & evidence

ORD record
ord-fc1aa90153f141789ea0a6c8dcf5e13c
Source dataset
uspto-grants-2013_10
Patent number
US08552181B2

Linked notes

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