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

HRID 215864Notes

Reaction equation

HRID 215864 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:17]([O:21][C:22](=[O:31])[NH:23][CH:24]1[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:5]1([O:4][C:2](=[O:3])[NH:30][CH:27]2[CH2:28][CH2:29][CH:24]([NH:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:31])[CH2:25][CH2:26]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Phenyl chloroformate (1 eq.) is added dropwise to a solution of pyridine in 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 RT for 1 hour. The reaction mixture is partitioned between (0.2 M) HCl(aq) and DCM. The organics are washed with water (×2), (sat)NaHCO3(aq) and brine. The 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 (×2), (sat)NaHCO3(aq) and brine
  3. dry with materialThe organics are dried (MgSO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1815da3bdf9d4b6eb32a12ce329c0cdf
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

Loading…