HCID 57467306, compound → Tert-butyl [7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

HRID 82863Notes

Reaction equation

HRID 82863 reaction equation
[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[N:19])[CH:16]=2)[CH2:11][CH2:10][CH:9]1[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.N.[Ni]>[NH2:19][CH2:18][C:15]1[CH:16]=[C:17]2[C:12]([CH2:11][CH2:10][CH:9]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH:8]2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 57467306HCID 57467306, compound

Product 1

HCID 57471193Tert-butyl [7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-yl]carbamateYield 100.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 1-benzyl-7-cyano-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (1.787 g, 4.93 mmol) was dissolved in THF (40 mL) and 7 N methanolic ammonia (40 mL). Raney nickel (0.422 g, 4.93 mmol) was added. The vessel was evacuated and filled with Hydrogen at atmospheric pressure. The mixture was stirred overnight at room temperature. The catalyst was filtered off on a celite pad and washed with 500 mL MeOH. Product was obtained as a crimson powder (1.813 g, 4.95 mmol, 100%) after evaporating the solvent.

Workup

  1. customThe vessel was evacuated
  2. additionfilled with Hydrogen at atmospheric pressure
  3. filtrationThe catalyst was filtered off on a celite pad
  4. washwashed with 500 mL MeOH

Sources & evidence

ORD record
ord-6cf86237fda544c1a2ce561a2ddc0aac
Source dataset
uspto-grants-2014_09
Patent number
US08846741B2

Reaction notes

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