racemic (R,S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate → (R,S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate

HRID 4695Notes

Reaction equation

HRID 4695 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:23]=[CH:22][C:10]([CH2:11][CH:12]2[C:21]3[CH:16]([CH2:17][CH2:18][CH2:19][CH:20]=3)[CH2:15][CH2:14][NH2+:13]2)=[CH:9][CH:8]=1>C(O)(C)C>[C:1]([O-:4])(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][C@@H:12]2[C:21]3[C@@H:16]([CH2:17][CH2:18][CH2:19][CH:20]=3)[CH2:15][CH2:14][NH2+:13]2)=[CH:22][CH:23]=1

Participants

3

Reactant 1

HCID 20151611racemic (R,S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate

Product 1

HCID 18611871(R,S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Sufficient racemic (R,S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate is dissolved in isopropanol to form a 52.6% by weight (R,S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate solution. The solution is seeded at 20° C. with about 1%, relative to the weight of the solution, of (S)-acetate and is stirred at 0° C. for 2 to 3 hours. The crystallized (S)-acetate is filtered off with suction and washed with tert.-butyl methyl ether.

Sources & evidence

ORD record
ord-02d791137985462297a555d94c554095
Source dataset
uspto-grants-1988_02
Patent number
US04727147

Reaction notes

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