tert-Butanol → HCID 86615516, compound

HRID 1098325Notes

Reaction equation

HRID 1098325 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]1CC(=C)C[O:10][C@@H:9]1[C:15]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=1[F:23])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:29]CC1.S(=O)(=O)(O)[O-].[Na+].C(OCC)(=O)C.[C:45]([OH:49])([CH3:48])([CH3:47])[CH3:46]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[OH:49][C:45]1([CH2:48][OH:29])[CH2:47][O:10][C@H:9]([C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=2[F:23])[C@@H:8]([NH:7][C:6](=[O:24])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:46]1

Participants

9

Reactant 5

HCID 6386tert-ButanolHCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 516919Sodium BisulfateHCID 86615515HCID 86615515, compound

Product 1

HCID 86615516HCID 86615516, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of tert-butyl[(2R,35)-5-methylene-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate (203 mg, 0.59 mmol) in tert-butyl alcohol (6 mL), acetone (3 mL) and water (1.5 mL) was added osmium tetroxide (0.113 mL of 2.5% solution in tert-butyl alcohol, 0.009 mmol). The resultant mixture was stirred at room temperature for 10 minutes and then treated with N-methylmorpholine N-oxide (92 mg, 0.79 mmol) and stirred. After two days, the reaction mixture was treated with aqueous sodium bisulfate solution (5 mL, 2.0N) followed after 10 min by ethyl acetate. The organic layer was washed successively with 2N hydrochloric acid and saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered and evaporated to yield tert-butyl [(2R,3S)-5-hydroxy-5-(hydroxymethyl)-2-(2,4,5-trifluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate which was used in the next step without further purification.

Workup

  1. washThe organic layer was washed successively with 2N hydrochloric acid and saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-fedb2acb5ef04aae9dafe0008595bdb5
Source dataset
uspto-grants-2012_03
Patent number
US08143289B2

Reaction notes

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