Methanol → HCID 131712716, compound

HRID 1065498Notes

Reaction equation

HRID 1065498 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][C:8](=[C:11]3[C:17]4[CH:18]=[C:19]([S:22][C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:21][C:16]=4[CH:15]=[CH:14][C:13]4[CH:27]=[CH:28][CH:29]=[CH:30][C:12]3=4)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.CO.[C:33]1([CH3:60])[CH:38]=[CH:37][C:36]([C:39]([C@:41]([C:57]([OH:59])=[O:58])([OH:56])[C@:42]([C:47]([C:49]2[CH:54]=[CH:53][C:52]([CH3:55])=[CH:51][CH:50]=2)=[O:48])([OH:46])[C:43]([OH:45])=[O:44])=[O:40])=[CH:35][CH:34]=1>C1(C)C=CC=CC=1>[C:33]1([CH3:60])[CH:38]=[CH:37][C:36]([C:39]([C@:41]([C:57]([OH:59])=[O:58])([OH:56])[C@:42]([C:47]([C:49]2[CH:50]=[CH:51][C:52]([CH3:55])=[CH:53][CH:54]=2)=[O:48])([OH:46])[C:43]([OH:45])=[O:44])=[O:40])=[CH:35][CH:34]=1.[CH:1]1([CH2:4][N:5]2[CH2:6][CH2:7][C:8](=[C:11]3[C:17]4[CH:18]=[C:19]([S:22][C:23]([F:25])([F:24])[F:26])[CH:20]=[CH:21][C:16]=4[CH:15]=[CH:14][C:13]4[CH:27]=[CH:28][CH:29]=[CH:30][C:12]3=4)[CH2:9][CH2:10]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3085262Piperidine, 1-(cyclopropylmethyl)-4-(3-((trifluoromethyl)thio)-5H-dibenzo(c,d)cyclohepten-5-ylidene)-, (-)-HCID 22860073(2R,3R)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid

Product 1

HCID 131712716HCID 131712716, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 387 g (0.906 mole) of (±)-1-cyclopropylmethyl-4-(3-trifluoromethylthio-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine (I) in 3870 ml of toluene containing 19 ml of methanol at room temperature (22°) was added 220 g (0.569 mole) of di-p-toluoyl-d-tartaric acid. A complete solution resulted within three minutes followed by rapid crystallization of the desired tartrate salt. The mixture was stirred vigorously at room temperature (23°) overnight. The crystalline product was collected by filtration, washed with 1 l. of toluene and dried under vacuum at room temperature to yield 355 g (86.5% physical yield) of (-)-1-cyclopropylmethyl-4-(3-trifluoromethylthio-5H-dibenzo[a,d]-cyclohepten-5-ylidene)piperidine di-p-toluoyl-d-tartrate, as the toluene solvate (II), m.p. 142°-146° dec., [α]D25 -91.3° (C=1, EtOH). A sample of this salt was converted to the free base and had a m.p. of 142°-145° dec., [α]D25 -58.0° (C=1, CH2Cl2) indicating 87% optical purity (O.P.).

Workup

  1. customA complete solution resulted within three minutes
  2. customfollowed by rapid crystallization of the desired tartrate salt
  3. filtrationThe crystalline product was collected by filtration
  4. washwashed with 1 l
  5. dry with materialof toluene and dried under vacuum at room temperature

Sources & evidence

ORD record
ord-7d29b47bec3d4800939e8e7e5a2ce778
Source dataset
uspto-grants-1982_05
Patent number
US04329469

Reaction notes

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