Phenyl chloroformate → (4-tert-Butoxycarbonylamino-cyclohexyl)-carbamic acid phenyl ester

HRID 1929774Notes

Reaction equation

HRID 1929774 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].N1C=CC=CC=1.C(Cl)Cl.[C:20]([O:24][C:25](=[O:34])[NH:26][CH:27]1[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]1)([CH3:23])([CH3:22])[CH3:21]>C(Cl)Cl>[C:5]1([O:4][C:2](=[O:3])[NH:33][CH:30]2[CH2:31][CH2:32][CH:27]([NH:26][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:34])[CH2:28][CH2:29]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamateHCID 21875418Pyridine methylene chloride

Product 1

HCID 67022954(4-tert-Butoxycarbonylamino-cyclohexyl)-carbamic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Phenyl chloroformate (1 eq.) is added dropwise to a solution of pyridine/DCM. The reaction mixture is cooled to 0° C. and a solution of (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (1 eq.) in DCM is added dropwise. The reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is partitioned between (0.2 M) HCl(aq) and DCM. The organics are washed with water, saturated sodium hydrogen carbonate solution and brine. The combined organics are dried (MgSO4), filtered and reduced in vacuo to yield the title compound.

Workup

  1. customThe reaction mixture is partitioned between (0.2 M) HCl(aq) and DCM
  2. washThe organics are washed with water, saturated sodium hydrogen carbonate solution and brine
  3. dry with materialThe combined organics are dried (MgSO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-2cd7314f62f34811bdfa54db01b94b13
Source dataset
uspto-grants-2012_05
Patent number
US08188100B2

Reaction notes

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