HCID 12690102, compound → HCID 20296477, compound

HRID 1389532Notes

Reaction equation

HRID 1389532 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]1[C:14]2([C:17]([OH:19])=O)[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]2)[CH2:10]1.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH:28]2[C:33]3([C:36]([OH:38])=O)[CH2:34][CH2:35][N:30]([CH2:31][CH2:32]3)[CH2:29]2)=[CH:23][CH:22]=1.[CH:39]([C:42]1[CH:43]=[C:44]([CH2:48][CH:49]2[C:54]3([C:57]([OH:59])=O)[CH2:55][CH2:56][N:51]([CH2:52][CH2:53]3)[CH2:50]2)[CH:45]=[CH:46][CH:47]=1)([CH3:41])[CH3:40].[Cl:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=1[CH2:67][CH:68]1[C:73]2([C:76]([OH:78])=O)[CH2:74][CH2:75][N:70]([CH2:71][CH2:72]2)[CH2:69]1.C1(CC2C3(C(O)=O)CCN(CC3)C2)C=CC=CC=1>>[CH3:1][C:2]1[C:3]2[CH2:8][CH:9]3[C:14]4([CH2:13][CH2:12][N:11]([CH2:10]3)[CH2:16][CH2:15]4)[C:17](=[O:19])[C:4]=2[CH:5]=[CH:6][CH:7]=1.[Br:20][C:21]1[CH:22]=[CH:23][C:24]2[CH2:27][CH:28]3[C:33]4([CH2:32][CH2:31][N:30]([CH2:29]3)[CH2:35][CH2:34]4)[C:36](=[O:38])[C:25]=2[CH:26]=1.[CH:39]([C:42]1[CH:47]=[CH:46][C:45]2[C:57](=[O:59])[C:54]34[CH2:55][CH2:56][N:51]([CH2:50][CH:49]3[CH2:48][C:44]=2[CH:43]=1)[CH2:52][CH2:53]4)([CH3:41])[CH3:40].[Cl:60][C:61]1[C:62]2[CH2:67][CH:68]3[C:73]4([CH2:72][CH2:71][N:70]([CH2:69]3)[CH2:75][CH2:74]4)[C:76](=[O:78])[C:63]=2[CH:64]=[CH:65][CH:66]=1

Participants

9

Reactant 5

HCID 12690102HCID 12690102, compoundHCID 20296478HCID 20296478, compoundHCID 20296480HCID 20296480, compoundHCID 20296483HCID 20296483, compoundHCID 20296485HCID 20296485, compound

Product 4

HCID 20296477HCID 20296477, compoundHCID 20296481HCID 20296481, compoundHCID 20296488HCID 20296488, compoundHCID 20296493HCID 20296493, compound

Procedure

Following essentially the same procedure but substituting 3-[(o-methylphenyl)methyl]-1-azabicyclo[2.2.2]-octane-4-carboxylic acid, 3-[(p-bromophenyl)methyl]-1-azabicyclo[2.2.2]octane-4-carboxylic acid, 3-[(m-isopropylphenyl)methyl]-1-azabicyclo[2.2.2]octane-4-carboxylic acid, and 3-[(o-chlorophenyl)methyl]-1-azabicyclo[2.2.2]octane-4-carboxylic acid for the 3-(phenylmethyl)-1-azabicyclo[2.2.2]octane-4-carboxylic acid above results in the formation of 9-methyl-3,4,10,10a-tetrahydro-2,4a-ethanobenz[g]isoquinolin-5(1H)-one, 7-bromo-3,4,10,10a-tetrahydro-2,4a-ethanobenz[g]isoquinolin-5(1H)-one, 8-isopropyl-3,4,10,10a-tetrahydro-2,4a-ethanobenz[g]isoquinolin-5(1H)-one, and 9-chloro-3,4,10,10a-tetrahydro-2,4a-ethanobenz[g]isoquinolin-5(1H)-one as their hydrochloride salts, respectively.

Sources & evidence

ORD record
ord-8e6c083ac4b74bc9ae4fe2eeeee4c17e
Source dataset
uspto-grants-1981_01
Patent number
US04244955

Reaction notes

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