1-Ethyl-1,2,3,6-tetrahydropyridine-4-methanol → 1'-Ethyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

HRID 1741087Notes

Reaction equation

HRID 1741087 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([OH:14])=[C:10](Br)[CH:11]=2)[CH2:6][CH2:5]1)(=O)C.[CH2:15]([N:17]1[CH2:22][CH:21]=[C:20]([CH2:23]O)[CH2:19][CH2:18]1)[CH3:16]>>[CH2:15]([N:17]1[CH2:22][CH2:21][C:20]2([C:10]3[C:9](=[CH:8][C:7]4[CH2:6][CH2:5][NH:4][C:12]=4[CH:11]=3)[O:14][CH2:23]2)[CH2:19][CH2:18]1)[CH3:16]

Participants

3

Reactant 2

HCID 218337641-Ethyl-1,2,3,6-tetrahydropyridine-4-methanolHCID 219483801-(6-Bromo-5-hydroxy-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Product 1

HCID 218337441'-Ethyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]Yield 45%

Procedure

This was prepared from 1-acetyl-6-bromo-2,3-dihydro-1H-indol-5-ol (Tetrahedron, 1973, 29 (8), 1115) and 1-ethyl-1,2,3,6-tetrahydropyridine-4-methanol (D108), following the procedure of Description 8 (alternative preparation), steps a), b), and c). This gave the title compound (overall yield: 45%) as a fine grey powder.

Workup

  1. customthe procedure of Description 8 (alternative preparation), steps a), b), and c)

Sources & evidence

ORD record
ord-c1b6dac6d55641e2af46456e7797745e
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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