Water → (R)-4-benzyl-3-((1S,2S,3S,5S)-2-(tert-butyldimethylsilyloxy)-bicyclo[3.1.0]hexane-3-carbonyl)oxazolidin-2-one

HRID 56403Notes

Reaction equation

HRID 56403 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@H:16]1[CH2:21][C@H:20]2[C@H:18]([CH2:19]2)[C@@H:17]1[OH:22])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])(=O)=O.O>ClCCl.CO>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([C@H:16]1[CH2:21][C@H:20]2[C@H:18]([CH2:19]2)[C@@H:17]1[O:22][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 67362377(R)-4-benzyl-3-((1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hexane-3-carbonyl)oxazolidin-2-one

Product 1

HCID 67361666(R)-4-benzyl-3-((1S,2S,3S,5S)-2-(tert-butyldimethylsilyloxy)-bicyclo[3.1.0]hexane-3-carbonyl)oxazolidin-2-oneYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (R)-4-benzyl-3-((1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hexane-3-carbonyl)oxazolidin-2-one (25 g, 83 mmol) and 2,6-lutidine (38.2 mL, 332 mmol) in dichloromethane (300 mL) was added tert-butyldimethylsilyl trifluoromethanesulfonate (47.6 mL, 207.5 mmol) at 0° C. under nitrogen. The resulting mixture was stirred at 0° C. for 30 minutes and then room temperature for 1 hour. After diluted with methanol (25 mL), the mixture was poured into water and extracted with ether (2×400 mL). The combined ether extracts were washed with brine, dried over sodium sulfate, filtered, concentrated and purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:8) to afford the title compound (29 g, 86%) as a colorless oil. MS (ES+) C23H33NO4Si requires: 415, found: 416 [M+H−H2O]+.

Workup

  1. waitroom temperature for 1 hour
  2. extractionextracted with ether (2×400 mL)
  3. washThe combined ether extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (ethyl acetate:petroleum ether=1:8)

Sources & evidence

ORD record
ord-f1c191679233479bb597d0cec111db2b
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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