Pyridine → HCID 178425906, compound

HRID 500074Notes

Reaction equation

HRID 500074 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.N1C=CC=CC=1.[CH3:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1.[Cl-].[NH4+]>ClCCl>[CH3:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([O:1][C@H:2]2[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]2)=[O:28])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 134054-Methylbenzoyl ChlorideHCID 25517Ammonium ChlorideHCID 178418329HCID 178418329, compound

Product 1

HCID 178425906HCID 178425906, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of t-butyl trans-4-hydroxycyclohexyl-carbamate (1.00 g) and pyridine (773 mg) in dichloromethane (40 ml) under ice-cooling was added a solution of 4-methylbenzoylchloride (754 mg) in dichloromethane (10 ml) over 10 minutes. The mixture was stirred overnight at room temperature, and then saturated aqueous ammonium chloride was added thereto. The mixture was extracted with chloroform, and the organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 1.30 g of t-butyl trans-[4-(4-methylphenylcarbonyloxy)cyclohexyl]-carbamate.

Workup

  1. temperaturecooling
  2. extractionThe mixture was extracted with chloroform
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)

Sources & evidence

ORD record
ord-e1a25669afcc4146892168853c2815c5
Source dataset
uspto-grants-2010_08
Patent number
US07767854B2

Reaction notes

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