Ethyl Acetate → Tert-butyl 2-(acetylamino)-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethylcarbamate

HRID 1880785Notes

Reaction equation

HRID 1880785 reaction equation
[Cl:1][C:2]1[C:3]([CH:12]([C:17]#[N:18])[NH:13][C:14](=[O:16])[CH3:15])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:19](=O)([O:25]C(C)(C)C)[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].[BH4-].[Na+].C(OCC)(=O)C>CO.O>[C:14]([NH:13][CH:12]([C:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:5][N:4]=1)[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:16])[CH3:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 66798198N-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl](cyano)methyl]acetamide

Product 1

HCID 66798280Tert-butyl 2-(acetylamino)-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethylcarbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5.00 g of N-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl](cyano)methyl]acetamide (0.018 mol), 7.86 g (0.036 mol) of diterbutyl carbonate, 4.28 g (0.018 mol) of nickel chloride (II)-hexahydrate are stirred in 25 mL of methanol at room temperature. 3.40 g (0.09 mol) of sodium borohydride are added portionwise. The reaction mixture is stirred overnight. 200 mL of ethyl acetate are added, followed by 50 mL of water. After separation, the aqueous phase id extracted twice 50 mL of ethyl acetate.

Workup

  1. customAfter separation
  2. extractionthe aqueous phase id extracted twice 50 mL of ethyl acetate

Sources & evidence

ORD record
ord-26723fc983824cc0ab776edaced59c6a
Source dataset
uspto-grants-2012_11
Patent number
US08318777B2

Reaction notes

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