Water → tert-butyl {2-[(1S,2R)-1,2-dihydroxypropyl]benzyl}carbamate

HRID 923483Notes

Reaction equation

HRID 923483 reaction equation
CS(N)(=O)=O.[OH2:6].[CH:7](/[C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:8]/[CH3:9].S([O-])([O-])(=[O:27])=S.[Na+].[Na+]>C(O)(C)(C)C>[OH:6][C@@H:7]([C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:19])[CH3:17])[C@H:8]([OH:27])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 72879MethanesulfonamideHCID 118318066tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate

Product 1

HCID 118318079tert-butyl {2-[(1S,2R)-1,2-dihydroxypropyl]benzyl}carbamate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a mixture of 3.30 g of AD mix-α, 200 mg of methanesulfonamide, 12.5 ml of tert-butyl alcohol, and 12.5 ml of water was added a solution of 500 mg of tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate in 5 ml of tert-butyl alcohol, followed by stirring at room temperature for 12 hours. To the reaction mixture was added sodium thiosulfate, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 449 mg of tert-butyl {2-[(1S,2R)-1,2-dihydroxypropyl]benzyl}carbamate.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-195099e262304b24bca2d9c68b8c5fec
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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