Tetrabutylammonium Fluoride Trihydrate → Carbamic acid, N-[(1R,2R,4S)-2-fluoro-4-hydroxycyclohexyl]-, 1,1-dimethylethyl ester, rel-

HRID 1423418Notes

Reaction equation

HRID 1423418 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].[Si]([O:39][C@@H:40]1[CH2:45][CH2:44][C@H:43]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[C@@H:42]([F:54])[CH2:41]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>>[F:54][C@H:42]1[CH2:41][C@H:40]([OH:39])[CH2:45][CH2:44][C@@H:43]1[NH:46][C:47](=[O:53])[O:48][C:49]([CH3:51])([CH3:50])[CH3:52]

Participants

3

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 131732234HCID 131732234, compound

Product 1

HCID 130835890Carbamic acid, N-[(1R,2R,4S)-2-fluoro-4-hydroxycyclohexyl]-, 1,1-dimethylethyl ester, rel-Yield 98.4%

Procedure

Tetrabutylammoniumfluoride trihydrate (11.9 g; 36.7 mmol) is added to a solution of tert-butyl [(1S*,2S*,4R*)-4-{[tert-butyl(diphenyl)silyl]oxy}-2-fluorocyclohexyl]carbamate (example C18; 8.7 g; 18.3 mmol). The reaction mixture is stirred over night at ambient temperature. The solvent is removed under reduced pressure. The residue is chromatographed on silica gel (cyclohexane/AcOEt—60:40 to 40:60) to yield 4.2 g of the title compound as colourless oil.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customThe residue is chromatographed on silica gel (cyclohexane/AcOEt—60:40 to 40:60)

Sources & evidence

ORD record
ord-2fdb44b17e0a4d51b4b8473b95173d92
Source dataset
uspto-grants-2015_01
Patent number
US08927557B2

Reaction notes

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