Tetrahydro-4H-pyran-4-one → 6-Methoxy-1-[4-(phenylmethoxy)benzyl]-2-(tetrahydropyran-4-yl)-1,2,3,4-tetrahydroisoquinoline

HRID 2119461Notes

Reaction equation

HRID 2119461 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=1)[NH:8][CH2:7][CH2:6]2.[O:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:15]=1)[N:8]([CH:31]1[CH2:32][CH2:33][O:28][CH2:29][CH2:30]1)[CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 129507356-Methoxy-1-[4-(phenylmethoxy)benzyl]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 234408336-Methoxy-1-[4-(phenylmethoxy)benzyl]-2-(tetrahydropyran-4-yl)-1,2,3,4-tetrahydroisoquinolineYield 78%

Procedure

The title compound was prepared as described in Example 14.C, using 6-methoxy-1-[4-(phenylmethoxy)benzyl]-1,2,3,4-tetrahydroisoquinoline (0.5 g, 1.39 mmol) and tetrahydro-4H-pyran-4-one (1.084 g, 10.8 mmol) to provide the title compound (0.479 g, 78% yield): ES−MS (m/z) 444 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-da8e606fd45c4c00b4323dcac0ea0ebb
Source dataset
uspto-grants-2004_02
Patent number
US06686351B2

Reaction notes

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