Water → HCID 178485965, compound

HRID 25566

Reaction equation

HRID 25566 reaction equation
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][OH:10])[CH2:5][CH2:4]1.[CH:11]1[C:16]([O:17][C:18](Cl)=[O:19])=[CH:15][CH:14]=[C:13]([Cl:21])[CH:12]=1.O>C[Si](C)(C)N[Si](C)(C)C>[Cl:21][C:13]1[CH:14]=[CH:15][C:16]([O:17][C:18](=[O:19])[N:2]([C@H:3]2[CH2:8][CH2:7][C@H:6]([CH2:9][OH:10])[CH2:5][CH2:4]2)[CH3:1])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1390594-Chlorophenyl chloroformateHCID 178484806HCID 178484806, compound

Product 1

HCID 178485965HCID 178485965, compound

Reagents, catalysts & solvents 1

HCID 13838HexamethyldisilazaneSolvent

Procedure

4.60 g (32.14 mmol) of trans-(4-Methylamino-cyclohexyl)-methanol was suspended in 85 ml hexamethyldisilazane and refluxed for 5 h. The solution was evaporated under reduced pressure and dissolved in 50 ml THF. 6.14 g (32.14 mmol) of 4-chlorophenylchloroformate were added slowly at 0° C. and stirred for 16 h at room temperature. 30 ml H2O were added and after 1 h the solvents were evaporated. The residue was extracted with water/Et2O (3×), the organic phases were washed with 10% NaCl, dried over Na2SO4 and evaporated to yield after flash-chromatography on silica gel (hexane/EtOAc 4:1 to 1:1) 5.48 g (57%) of trans-(4-Hydroxymethyl-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, MS: 298 (MH+, 1Cl).

Workup

  1. temperaturerefluxed for 5 h
  2. customThe solution was evaporated under reduced pressure
  3. dissolutiondissolved in 50 ml THF
  4. customwere evaporated
  5. extractionThe residue was extracted with water/Et2O (3×)
  6. washthe organic phases were washed with 10% NaCl
  7. dry with materialdried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-d6ce6f00a8b94d138694ffea83c0e1e0
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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