Triethylamine → 3-(3,4-Difluorophenyl)4-(ethoxycarbonylamino)-1-butanol

HRID 2185907Notes

Reaction equation

HRID 2185907 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][CH2:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=1)[CH2:10][CH2:11][OH:12].C(N(CC)CC)C>C(Cl)Cl>[F:20][C:15]1[CH:14]=[C:13]([CH:9]([CH2:8][NH:7][C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH2:10][CH2:11][OH:12])[CH:18]=[CH:17][C:16]=1[F:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 224526374-Amino-3-(3,4-difluorophenyl)-1-butanol

Product 1

HCID 224526773-(3,4-Difluorophenyl)4-(ethoxycarbonylamino)-1-butanolYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chloroformate (3.9 mL, 40.8 mmol) was added dropwise to a stirred cooled (−40° C.) solution of 4-amino-3-(3,4-difluorophenyl)-1-butanol (7.45 g, 37 mmol) and triethylamine (5.94 mL, 42.6 mmol) in DCM (180 mL). The solution was stirred at room temperature for 30 min and at room temperature overnight. The material was washed twice with 1N HCl, twice with saturated sodium bicarbonate; dried (Na2SO4), filtered and the solvent removed to provide the title compound (8.85 g, 88%) as a yellow oil. 1H-NMR (CDCl3) δ 1.18-1.23 (t, 3H, CH) 1.72-1.98 (m, 3H) 2.96-3.00 (m, 1H, CH) 3.24-3.29 (m, 1H, CH) 3.45-4.04 (m, 3H, CH), 4.06-4.14 (m, 2H, CH) 4.66 (br. s, 1H, OH or NH) 6.91-7.37 (m, 3H, ArH). MS m/z 274 (M+H).

Workup

  1. washThe material was washed twice with 1N HCl, twice with saturated sodium bicarbonate
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent removed

Sources & evidence

ORD record
ord-9f2baada93884e98bedf46a8e507599e
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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