HCID 57471190, compound → Tert-butyl [7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

HRID 510507Notes

Reaction equation

HRID 510507 reaction equation
Cl[C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=3)[CH2:10][CH2:9][CH:8]2[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:4][CH:3]=1>CO.[Ni]>[NH2:18][CH2:17][C:14]1[CH:15]=[C:16]2[C:11]([CH2:10][CH2:9][CH:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH:7]2[CH2:6][C:5]2[CH:4]=[CH:3][CH:2]=[CH:28][CH:27]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 57471190HCID 57471190, compound

Product 1

HCID 57471193Tert-butyl [7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Tert-butyl [1-(4-chlorobenzyl)-7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate (52 mg, 0.131 mmol, cf. example 30d) were dissolved in methanol (5 mL). Raney nickel (about 30 mg) was added and the reaction mixture was stirred at room temperature for 4 h under an atmosphere of hydrogen. The catalyst was removed by filtration. The solvent was evaporated in vacuo. The crude product was used without further purification for the next step. Yield: 32 mg (0.087 mmol, 67%).

Workup

  1. customThe catalyst was removed by filtration
  2. customThe solvent was evaporated in vacuo
  3. customThe crude product was used without further purification for the next step

Sources & evidence

ORD record
ord-e655ef7eafdf4a4cbf949cf6b56528bd
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

Loading…