Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (8aS,12aS,13aS)-2,3-methylenedioxy-5,6,8a,9,10,11,12,12a,13,13a-decahydroisoquino[2,1-g][1,6]naphthyridin-8-one

HRID 484393Notes

Reaction equation

HRID 484393 reaction equation
CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=[O:8].[CH3:16][O:17][C:18]1[CH:35]=[CH:34][C:33]2[C@H:32]3[N:23]([C:24](=[O:36])[C@@H:25]4[C@H:30]([CH2:31]3)[NH:29][CH2:28][CH2:27][CH2:26]4)[CH2:22][CH2:21][C:20]=2[CH:19]=1>>[CH2:16]1[O:17][C:18]2=[CH:19][C:20]3[CH2:21][CH2:22][N:23]4[C@H:32]([C:33]=3[CH:34]=[C:35]2[O:8]1)[CH2:31][C@H:30]1[C@H:25]([CH2:26][CH2:27][CH2:28][NH:29]1)[C:24]4=[O:36]

Participants

3

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 9838835(8aS,12aS,13aS)-3-methoxy-5,6,8a,9,10,11,12,12a,13,13a-decahydroisoquino[2,1-g][1,6]naphthyridin-8-one

Product 1

HCID 14881411(8aS,12aS,13aS)-2,3-methylenedioxy-5,6,8a,9,10,11,12,12a,13,13a-decahydroisoquino[2,1-g][1,6]naphthyridin-8-one

Procedure

Similarly, replacing the d-10-camphorsulfonic acid salt of (8aS,12aS,13aS)-3-methoxy-5,6,8a,9,10,11,12,12a,13,13a-decahydroisoquino[2,1-g][1,6]naphthyridin-8-one with compounds of formula (IA), obtained, for example, as described in Example 4C, and following the procedures of Example 5A above, the corresponding compounds of formula (I) as a free base are made.

Sources & evidence

ORD record
ord-c3857a2982e04b1c9f100f1c73783989
Source dataset
uspto-grants-1993_07
Patent number
US05231181

Reaction notes

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