Diisopropylethylamine → HCID 178485970, compound

HRID 25544

Reaction equation

HRID 25544 reaction equation
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.[CH:10]1[C:15]([O:16][C:17](Cl)=[O:18])=[CH:14][CH:13]=[C:12]([Cl:20])[CH:11]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:20][C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17](=[O:18])[N:2]([C@H:3]2[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]2)[CH3:1])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 178484843HCID 178484843, compound

Product 1

HCID 178485970HCID 178485970, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 16.1 g (124.7 mmol) trans-4-methylamino-cyclohexanol in 40 ml CH2Cl2, 18.3 ml (130.9 mmol, 1.05 eq) 4-chlorophenylchloroformate and 22.4 ml (130.9 mmol, 1.05 eq) Huenig's base were added at 0° C. The solution was stirred at RT over night, diluted, and washed with 1M HCl, sat. aqueous NaHCO3 solution. The organic phase was dried over MgSO4. Column chromatography on silica gel with EtOAc:hexane 1:1 yielded 32.2 g (91%) trans-(4-Hydroxy-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester as white solid, MS: 283 (M, 1Cl).

Workup

  1. additiondiluted
  2. washwashed with 1M HCl, sat. aqueous NaHCO3 solution
  3. dry with materialThe organic phase was dried over MgSO4

Sources & evidence

ORD record
ord-d0628b29439549319592cdc359ca3e85
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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