Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate

HRID 451758Notes

Reaction equation

HRID 451758 reaction equation
[F:1][C:2]1([CH2:8][C@H:9]2[CH2:13][O:12]C(C)(C)[N:10]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CO>[F:1][C:2]1([CH2:8][C@H:9]([NH:10][C:16](=[O:17])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:13][OH:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 59201498(S)-tert-butyl 4-((1-fluorocyclohexyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 68713243(S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamateYield 28.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-tert-butyl 4-((1-fluorocyclohexyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (1.1 g, 3.50 mmol, 1.0 equiv) was dissolved in methanol (30 mL). To this mixture was added camphorsulfonic acid (202 mg, 0.875 mmol, 0.5 equiv) and the solution was stirred at rt for 3 h. After this time the starting material was consumed. Satd aq NaHCO3 was added and the methanol was removed in vacuo. The aqueous residue was extracted with EtOAc (3×10 mL) and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Flash chromatography on silica, eluting with 0-47% EtOAc in hexanes, afforded (S)-tert-butyl 1-(1-fluorocyclohexyl)-3-hydroxypropan-2-ylcarbamate (275 mg).

Workup

  1. customAfter this time the starting material was consumed
  2. additionSatd aq NaHCO3 was added
  3. customthe methanol was removed in vacuo
  4. extractionThe aqueous residue was extracted with EtOAc (3×10 mL)
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. washFlash chromatography on silica, eluting with 0-47% EtOAc in hexanes

Sources & evidence

ORD record
ord-ce8de18e6b4b4148b49ea5d57474ec36
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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