HCID 178523817, compound → Benzyl (4-oxocyclohexyl)carbamate

HRID 1765326Notes

Reaction equation

HRID 1765326 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 178523817HCID 178523817, compound

Product 1

HCID 14615292Benzyl (4-oxocyclohexyl)carbamateYield 78%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Procedure

To a stirred solution of trans-4-benzyloxycarbonylaminocyclohexanol (21.5 g, 86.3 mmol) in acetic acid (160 mL) at room temperature under nitrogen was added chromium trioxide (8.63 g, 86.3 mmol). After 1 d, the reaction mixture was evaporated under vacuum to yield a residue. The residue was suspended in acetone and filtered through a plug of Celite®. The filtrate was evaporated to obtain a green solid. The green solid was purified by silica gel chromatography (eluted with 5% methanol in methylene chloride) to obtain the title compound (16.65 g, 78%) as an off-white solid. 13C NMR (400 MHz, CDCl3) δ 209.6, 155.8, 136.2, 128.5, 128.2, 128.1, 66.8, 47.9, 38.8, 32.1. 1H NMR (400 MHz, CDCl3) δ 7.34 (m, 5H), 5.09 (s, 2H), 4.84 (br s, 1H), 3.97 (s, 1H), 2.38 (m, 4H), 2.20 (m, 2H), 1.68 (m, 2H). HPLC/MS [M+H]+, 248.

Workup

  1. customthe reaction mixture was evaporated under vacuum
  2. customto yield a residue
  3. filtrationfiltered through a plug of Celite®
  4. customThe filtrate was evaporated
  5. customto obtain a green solid
  6. customThe green solid was purified by silica gel chromatography (eluted with 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-34bb337832cc443d96eb900914f6d363
Source dataset
uspto-grants-2007_06
Patent number
US07226942B2

Reaction notes

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