2,3-dihydro-2-methyl-7-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-pyrrolo[1,2-a]indol-1-one → 1,2,3,4Tetrahydro-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]cyclopent[b]indol-1-one

HRID 22289Notes

Reaction equation

HRID 22289 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([CH:14]=[C:15]3[CH2:26][C:18]4[NH:19][C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=5[C:17]=4[C:16]3=[O:27])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1(CC2CCN(CC3C=CC=CC=3)CC2)CN2C3C=CC(OC)=CC=3C=C2C1=O>C(OCC)(=O)C.C(O)C>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH:15]3[CH2:26][C:18]4[NH:19][C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=5[C:17]=4[C:16]3=[O:27])[CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 199278542,3-dihydro-2-methyl-7-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-pyrrolo[1,2-a]indol-1-oneHCID 540822371,2,3,4-Tetrahydro-2-[[1-(phenylmethyl)-4-piperidinyl]methylene]cyclopent[b]indol-1-one

Product 1

HCID 199277931,2,3,4Tetrahydro-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]cyclopent[b]indol-1-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

the title compound of Example 42 (176 mg, 0.5 mmol) was dissolved in a mixture solvents of ethyl acetate (31 ml) and ethanol (31 ml) and treated with PtO 2 (23 mg) and hydrogenated at 35 psi at r.t. for 2 hours. The mixture was filtered through diatomaceous earth (Celite (trademark)) and the filtrate was concentrated to give compound the title compound as off-white solid. 1HNMR (CDCl3)δ 1.3-1.65 (m, 4H), 1.65-1.8 (m, 2H), 1.9-2.1 (m, 3H), 2.65 (dd, 1H), 2.9-3.1 (m, 3H), 3.2 (dd, 1H), 3.55 (s, 2H), 7.15-7.4 (m, 8H), 7.9 (dd, 1H), 9.15 (s, 1H) ppm.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth (Celite (trademark))
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b27ea2c896a2414ebd672ed7f92ac7fd
Source dataset
uspto-grants-1995_06
Patent number
US05428043

Reaction notes

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