HCID 12884442, compound → HCID 12884446, compound

HRID 1277524Notes

Reaction equation

HRID 1277524 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:17][CH2:16][CH2:15][C:14]2=[CH:13][N:12]([CH3:18])[CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1.COC1C=C([C@@]23CCC[C@H]2CN(C)CC3)C=CC=1>[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[CH2:17][CH2:16][CH2:15][C@@H:14]2[CH2:13][N:12]([CH3:18])[CH2:11][CH2:10]3)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 12884442HCID 12884442, compoundHCID 86737844HCID 86737844, compound

Product 1

HCID 12884446HCID 12884446, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

Following the procedure set forth in Example 5, 4a-(3-methoxyphenyl)-2-methyl-3,4,4a,5,6,7-hexahydro-2-pyrindine was hydrogenated over platinum oxide to provide a 60:40 mixture of trans-4a-(3-methoxyphenyl)-2-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine and the corresponding cis-isomer. The trans isomer was crystallized asthe picrate salt. The cis isomer was isolated as the free base, namely cis-4a-(3-methoxyphenyl)-2-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine; M.P.=40°-43° C.

Workup

  1. customto provide
  2. customThe trans isomer was crystallized asthe picrate salt

Sources & evidence

ORD record
ord-b4e03d1854694b4da6e55e6ef1f436f2
Source dataset
uspto-grants-1981_07
Patent number
US04277608

Reaction notes

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