tert-Butyl 7-cyano-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate → tert-Butyl 7-(aminomethyl)-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 1850889Notes

Reaction equation

HRID 1850889 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:10]2[C:13]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1)#[N:2]>CO.[Ni]>[NH2:2][CH2:1][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:10]2[C:13]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:14][CH2:15][CH2:16]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 58246239tert-Butyl 7-cyano-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 58246415tert-Butyl 7-(aminomethyl)-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 7-cyano-1-[1-(pyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate (169 mg, 0.434 mmol) was dissolved in methanol (15 mL) under an atmosphere of nitrogen. Raney nickel (100 mg) was added and the reaction mixture stirred at room temperature under an atmosphere of hydrogen for 9 hours. The catalyst was removed by filtration. The filtrate was concentrated in vacuo and the crude product was purified by flash chromatography (silica, dichloromethane, methanol). Yield: 103 mg (0.262 mmol, 60%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe crude product was purified by flash chromatography (silica, dichloromethane, methanol)

Sources & evidence

ORD record
ord-18a93f764dca498793e9417d9d61040e
Source dataset
uspto-grants-2015_02
Patent number
US08957089B2

Reaction notes

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