Pyridine → (4-Pyrrolidin-1-ylmethyl-3-trifluoromethyl-phenyl)-carbamic acid phenyl ester

HRID 2264603Notes

Reaction equation

HRID 2264603 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=2[C:14]([F:17])([F:16])[F:15])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+].O.[CH3:31][CH2:32][O:33][C:34](C)=[O:35]>C1COCC1>[C:32]1([O:33][C:34](=[O:35])[NH:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[C:8]([C:14]([F:15])([F:16])[F:17])[CH:9]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:31]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 2735133Sodium Carbonate MonohydrateHCID 598642004-[(Pyrrolidin-1-yl)methyl]-3-(trifluoromethyl)aniline

Product 1

HCID 67530371(4-Pyrrolidin-1-ylmethyl-3-trifluoromethyl-phenyl)-carbamic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 49 μl (0.39 mMol) phenyl chloroformiate in 1.5 ml THF is cooled to −70° C. Then a solution of 81 mg (0.33 mMol) 4-pyrrolidin-1-ylmethyl-3-trifluoromethyl-phenylamine and 0.3 ml pyridine in 1.5 ml THF is added dropwise. After 1 h, it is poured into a mixture of 20 g ice, 40 ml sat. Na2CO3/water 1:3 and 40 ml EtOAc. The aqueous layer is separated off and extracted 2× with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated to the title compound: MS: [M+1]+=365; HPLC: AtRet=11.1.

Workup

  1. customThe aqueous layer is separated off
  2. extractionextracted 2× with EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to the title compound

Sources & evidence

ORD record
ord-8cb5ae966bff4cabba5f33a2407dda32
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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