8-Methoxy-2-cyanomethyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole → 8-Methoxy-2-(2-aminoethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 5348

Reaction equation

HRID 5348 reaction equation
[CH3:1][O:2][CH:3]1[CH:14]2[CH:10]([CH2:11][N:12]([CH2:15][C:16]#[N:17])[CH2:13]2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2>CO.N.[Rh]>[CH3:1][O:2][CH:3]1[CH:14]2[CH:10]([CH2:11][N:12]([CH2:15][CH2:16][NH2:17])[CH2:13]2)[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2

Participants

5

Reactant 1

HCID 197956668-Methoxy-2-cyanomethyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 197956898-Methoxy-2-(2-aminoethyl)-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrroleYield 95.3%

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

The product from Example 16 (1.00 g) was dissolved in 90 ml methanol and 10 ml anhydrous ammonia. 0.100 g 5% Rh/Al2O3 was added and the reaction was hydrogenated at 4 atm for 4 h. The reaction was filtered and the solvent removed to yield 0.97 g of the desired product as a colorless oil. NMR (CDCl3) δ2.20-2.61 (m, 3H), 2.66-3.45 (m, 8H), 3.82 (s, 3H), 3.89 (m, 1H), 6.67 (d, 1H), 6.78 (d, 1H), 7.14 (t, 1H).

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent removed

Sources & evidence

ORD record
ord-b8624136abe04640a5b5ceda72784b10
Source dataset
uspto-grants-1993_09
Patent number
US05244888

Linked notes

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