L-Tartaric acid → D-Tartaric acid

HRID 129426

Reaction equation

[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([CH2:11][CH2:12][CH2:13][NH:14]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([OH:26])(=[O:25])[C@@H:18]([C@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19].[C:27]([C@@H:30]([C@H:32]([C:34]([OH:36])=[O:35])[OH:33])[OH:31])([OH:29])=[O:28].C(N1C[C@H]2[C@H](CCCN2)C1)C1C=CC=CC=1.C([C@@H]([C@H](C(O)=O)O)O)(O)=O.C(N1C[C@@H]2[C@@H](CCCN2)C1)C1C=CC=CC=1>CN(C)C=O>[C:22]([C@H:20]([C@@H:18]([C:17]([OH:26])=[O:25])[OH:19])[OH:21])([OH:24])=[O:23].[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@@H:10]([CH2:11][CH2:12][CH2:13][NH:14]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:34]([OH:36])(=[O:35])[C@H:32]([C@@H:30]([C:27]([OH:29])=[O:28])[OH:31])[OH:33]

Participants

Conditions

Temperature: 18 °C

Procedure

73.6 g (0.34 mol) of cis-8-benzyl-2,8-diazabicyclo[4.3.0]nonane dissolved in 111 ml of dimethylformamide is added a drop at a time to a solution of 102.9 g (0.685 mol) of L(+)-tartaric acid in 343 ml of dimethylformamide. The batch is seeded with [R,R]-8-benzyl-2,8-diazabicyclo[4.3.0]nonane L-tartrate and gradually cooled to an interior temperature of 18° C. The crystals are suctioned off and the filtrate seeded with [S,S]-8-benzyl-2,8-diazabicyclo[4.3.0]-nonane L-tartrate and agitated until it crystallizes completely. ([S,S]-8-benzyl-2,8-diazabicyclo[4.3.0]nonane D-tartrate can be obtained from the mother liquor subsequent to concentration and release of the base by purification with D(-)-tartaric acid as described for Method I.) The product is suctioned off, washed with dimethylformamide and isopropyl alcohol, and dried in the air. The crystals are recrystallized from 88% ethanol. 52 g of [S,S]-8-benzyl-2,8-diazabicyclo[4.3-O]nonane L-tartrate trihydrate are obtained.

Workup

customcrystallizes completely

Sources & evidence

ORD record: ord-a8f57c9f8141442fa246a3b1ec4c906e
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05468742

Linked notes

Loading…