2-Benzyl-8-methoxy-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole hydrochloride → 8-Methoxy-1,2,3,3a,8,8a-hexahydro-indeno[1,2-c]pyrrole hydrochloride

HRID 5346Notes

Reaction equation

HRID 5346 reaction equation
[ClH:1].C([N:9]1[CH2:13][CH:12]2[CH:14]([O:21][CH3:22])[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[CH:11]2[CH2:10]1)C1C=CC=CC=1>CO.[Pd]>[ClH:1].[CH3:22][O:21][CH:14]1[CH:12]2[CH:11]([CH2:10][NH:9][CH2:13]2)[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=2

Participants

4

Reactant 1

HCID 197957022-Benzyl-8-methoxy-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole hydrochloride

Product 1

HCID 678559868-Methoxy-1,2,3,3a,8,8a-hexahydro-indeno[1,2-c]pyrrole hydrochlorideYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product from Example 5 (4.90 g) was hydrogenated with 2.45 g 20% Pd/C in 200 ml methanol at 3 atm, affording 3.17 g of the desired product, mp: 208°-209° C. NMR (d6DMSO/D2O) δ2.83 (m, 2H), 3.14-3.29 (m, 3H), 3.46 (dd, 1H), 3.55 (dd, 1H), 3.80 (s, 3H), 3.95 (m, 1H), 6.85 (d, 2H), 7.25 (t, 1H).

Sources & evidence

ORD record
ord-7fb126bc875649eb8713b2431fdb30fa
Source dataset
uspto-grants-1993_09
Patent number
US05244888

Reaction notes

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