Sodium borohydride → Tert-butyl 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]butylcarbamate

HRID 655920Notes

Reaction equation

HRID 655920 reaction equation
[Cl:1][C:2]1[C:3]([CH:12]([CH2:15][CH3:16])[C:13]#[N:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:17](=O)([O:23]C(C)(C)C)[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].[BH4-].[Na+]>CO>[Cl:1][C:2]1[C:3]([CH:12]([CH2:15][CH3:16])[CH2:13][NH:14][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 66798076HCID 66798076, compound

Product 1

HCID 23078240Tert-butyl 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]butylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

189 g of 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]butanenitrile (0.758 mol), 331 g (1.51 mol) of diterbutyl carbonate, 198 g (0.834 mol) of nickel chloride (II)-hexahydrate are stirred in 2 L of methanol at room temperature. 200.6 g (5.31 mol) of sodium borohydride are added portionwise. After 3 hours of stirring, the reaction mixture is filtered over Supercel, 2 L of ethyl acetate are added, followed by 1.5 L of an aqueous solution of sodium bicarbonate.

Workup

  1. filtrationthe reaction mixture is filtered over Supercel, 2 L of ethyl acetate
  2. additionare added

Sources & evidence

ORD record
ord-644c13b859444aee990f0720cf064ac9
Source dataset
uspto-grants-2011_12
Patent number
US08071627B2

Reaction notes

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