Ditoluoyltartaric acid, (+)- → (1S)-1-(2-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline (2s,3s)-2,3-bis[(4-methylbenzoyl)oxy]succinate

HRID 2383027Notes

Reaction equation

HRID 2383027 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][NH:10]1.[CH3:19][C:20]1[CH:46]=[CH:45][C:23]([C:24]([O:26][C@@H:27]([C@H:31]([O:35][C:36](=[O:44])[C:37]2[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=2)[C:32]([OH:34])=[O:33])[C:28]([OH:30])=[O:29])=[O:25])=[CH:22][CH:21]=1>C(#N)C>[CH3:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:26][C@@H:27]([C@H:31]([O:35][C:36](=[O:44])[C:37]2[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][CH:42]=2)[C:32]([OH:34])=[O:33])[C:28]([OH:30])=[O:29])=[O:25])=[CH:45][CH:46]=1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C@@H:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][NH:10]1

Participants

4

Reactant 2

HCID 263211Ditoluoyltartaric acid, (+)-HCID 242573611-(2-Methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 131729938(1S)-1-(2-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline (2s,3s)-2,3-bis[(4-methylbenzoyl)oxy]succinateYield 75.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline (8.227 g) and (2S,3S)-2,3-bis[(4-methybenzoyl)oxy]succinic acid (13.282 g) were dissolved with stirring in acetonitrile (246 mL) at 70° C. The mixture was slowly cooled with stirring. The resulting crystal was collected by filtration, washed with acetonitrile, and dried under reduced pressure to obtain (1S)-1-(2-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline (2S,3S)-2,3-bis[(4-methylbenzoyl)oxy]succinate (16.193 g).

Workup

  1. temperatureThe mixture was slowly cooled
  2. filtrationThe resulting crystal was collected by filtration
  3. washwashed with acetonitrile
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-31e0d92887f84727a80c929ebab8a774
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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