4-Chlorophenyl chloroformate → HCID 178501224, compound

HRID 2118251Notes

Reaction equation

HRID 2118251 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][CH3:12])[CH2:7][CH2:6]1)=[O:4].Cl.[CH:14]1[C:19]([O:20][C:21](Cl)=[O:22])=[CH:18][CH:17]=[C:16]([Cl:24])[CH:15]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:21]([O:20][C:19]2[CH:18]=[CH:17][C:16]([Cl:24])=[CH:15][CH:14]=2)=[O:22])[CH3:12])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 1390594-Chlorophenyl chloroformateHCID 178484819HCID 178484819, compound

Product 1

HCID 178501224HCID 178501224, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2.12 g (10.21 mmol) of trans-4-methylamino-cyclohexanecarboxylic acid methyl ester•HCl was dissolved in 30 mL of pyridine, treated at 0° C. with 1.57 mL (11.23 mmol, 1.1 eq) of 4-chlorophenylchloroformate and stirred for 22 h at RT. The solution was evaporated and partitioned between EtOAc (×3)/aqueous 1M HCl. The organic phases were washed once with aqueous 10% NaCl, dried over Na2SO4 and evaporated to yield 3.41 g (90%) of trans-4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexane-carboxylic acid methyl ester, MS: 326 (MH+, 1Cl).

Workup

  1. customThe solution was evaporated
  2. custompartitioned between EtOAc (×3)/aqueous 1M HCl
  3. washThe organic phases were washed once with aqueous 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-40e340107969480d8a2b9c5201b93c4e
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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