Benzyl chloroformate → HCID 67152002, compound

HRID 1497956Notes

Reaction equation

HRID 1497956 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[F:12][C:13]1([F:24])[CH2:18][CH2:17][CH:16]([CH2:19][NH:20][CH2:21][CH2:22][OH:23])[CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:5]([O:4][C:2](=[O:3])[N:20]([CH2:19][CH:16]1[CH2:15][CH2:14][C:13]([F:12])([F:24])[CH2:18][CH2:17]1)[CH2:21][CH2:22][OH:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 671520472-[[(4,4-Difluorocyclohexyl)methyl]amino]ethanol

Product 1

HCID 67152002HCID 67152002, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl chloroformate (4.8 mL, 33.2 mmol) was added to a solution of 2-[(4,4-difluoro-cyclohexylmethyl)-amino]-ethanol (6.41 g, 33.2 mmol) and DIPEA (5.8 mL) in DCM (200 mL) and the reaction mixture was stirred for 1 h. The reaction mixture was washed with 0.1 N HCl (150 mL) and then with water (100 mL). The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and concentrated to give the title product as a clear oil (9.1 g) which partially crystallized overnight.

Workup

  1. washThe reaction mixture was washed with 0.1 N HCl (150 mL)
  2. customThe organic layer was collected
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6fa2445110684630a4fb3342aa82cef3
Source dataset
uspto-grants-2015_12
Patent number
US09199993B2

Reaction notes

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