Water → HCID 178485998, compound

HRID 25563Notes

Reaction equation

HRID 25563 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[N:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([O:18][Si](C(C)(C)C)(C)C)[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+:32](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[NH2:32][C:15]1([OH:18])[CH2:16][CH2:17][CH2:12][CH2:13][CH2:14]1.[CH2:1]([O:8][C:9](=[O:26])[N:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 178486000HCID 178486000, compound

Product 2

HCID 147398371-Aminocyclohexan-1-olHCID 178485998HCID 178485998, compoundYield 180.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3.1 g (8 mmol) trans-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-methyl-carbamic acid benzyl ester in 20 ml THF, 10.3 ml (1M, 10.3 mmol, 1.3 eq) Tetrabutylammonium fluoride in THF were added at 6° C. and the mixture was stirred at RT for 2 days. Water was added and the phases were separated and the inorganic phase was extracted with ether and EtOAc. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated. Column chromatography on silica gel with a gradient EtOAc:hexane 1:4-EtOAc yielded 1.9 g 1.9 g (92%) trans-(4-Hydroxy-cyclohexyl)-methyl-carbamic acid benzyl ester as orange oil, MS: 263 (M).

Workup

  1. customthe phases were separated
  2. extractionthe inorganic phase was extracted with ether and EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-f22eaee395a747fdac90cb59abf0b2f3
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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