Benzyl chloroformate → Cbz-trans-4-(aminomethyl)cyclohexanecarboxylic acid

HRID 729209Notes

Reaction equation

HRID 729209 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>[OH-].[Na+].O>[C:17]1([CH2:16][O:15][C:13]([NH:1][CH2:2][CH:3]2[CH2:4][CH2:5][CH:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]2)=[O:14])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 178511262HCID 178511262, compound

Product 1

HCID 3723035Cbz-trans-4-(aminomethyl)cyclohexanecarboxylic acidYield 96.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of trans-4-(aminomethyl)cyclohexanecarboxylic acid (10 g, 63.6 mmol, Aldrich) in 2N aqueous NaOH (65 ml) at 0° C. was added benzyl chloroformate (11.9 g, 70 mmol, Aldrich) and the reaction temperature was maintained below 10° C. The cloudy mixture was stirred at RT for 0.5 h. It was then diluted with H2O (100 ml). The clear solution was washed with ether (3×80 ml). The pH of the aqueous layer was adjusted to 2 by adding 6N HCl. The precipitates were filtered and dried in vacuo. 17.8 g of 23 was obtained as a white solid.

Workup

  1. temperaturethe reaction temperature was maintained below 10° C
  2. washThe clear solution was washed with ether (3×80 ml)
  3. additionby adding 6N HCl
  4. filtrationThe precipitates were filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-4d3827e9f07a4901b599d9d062a73bc6
Source dataset
uspto-grants-2009_09
Patent number
US07582280B2

Reaction notes

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