Potassium Hydroxide → Dinapsoline, (S)(-)

HRID 8712

Reaction equation

HRID 8712 reaction equation
C1[O:20][C:19]2[C:3](=[C:4]3[C:16](=[CH:17][CH:18]=2)[CH:8]2[CH2:9][NH:10][CH2:11][C:12]4[CH:13]=[CH:14][CH:15]=[C:6]([C:7]=42)[CH2:5]3)[O:2]1.C([C@](C(O)=O)(O)[C@](C(=O)C1C=CC=CC=1)(O)C(O)=O)(=O)C1C=CC=CC=1.[OH-].[K+].C(O)(=O)[C@H]([C@@H](C(O)=O)O)O>C(O)C.CO>[OH:2][C:3]1[C:19]([OH:20])=[CH:18][CH:17]=[C:16]2[C:4]=1[CH2:5][C:6]1[C:7]3[C@@H:8]2[CH2:9][NH:10][CH2:11][C:12]=3[CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 439655D-Tartaric acidHCID 11207814(+/-)-8,9-Methylenedioxy-2,3,7,11b-tetrahydro-1H-napth[1,2,3-de]isoquinolineHCID 12362977Di-benzoyl-d-tartaric acid

Product 1

HCID 10923047Dinapsoline, (S)(-)

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

A solution of racemic (±)-8,9-methylenedioxy-2,3,7,11b-tetrahydro-1H-napth[1,2,3-de]isoquinoline (3.0 gm, 11.3 mmol) in 100 mL of 95% ethyl alcohol at room temperature was mixed with a warm solution of (+)-dibenzoyl-D-tartaric acid in 40 mL of 95% ethyl alcohol. The solution was allowed to stand at room temperature for 4 hours and the grayish off-white crystals were collected by filtration and subsequently dried in a vacuum oven at 35° C. to give 1.3 gm (melting point: 175–176° C., 35.7%). The enantiomeric purity was determined by the same chiral HPLC conditions described above in Example 8: the salt was neutralized with 2M potassium hydroxide solution and the organic materials extracted with methylene chloride. The organic layers were combined and concentrated under reduced pressure to give a white solid which was redissolved in methanol prior to injection into HPLC Chiral column. The ratio of the second peak to the first was determined to be greater than 40:1. The identical resolution may also be. carried out using the unnatural D-tartaric acid. Melting points are uncorrected for the desired tartaric salts of the title compound.

Workup

  1. filtrationthe grayish off-white crystals were collected by filtration
  2. customsubsequently dried in a vacuum oven at 35° C.
  3. customto give 1.3 gm (melting point: 175–176° C., 35.7%)
  4. extractionthe organic materials extracted with methylene chloride
  5. concentrationconcentrated under reduced pressure
  6. customto give a white solid which

Sources & evidence

ORD record
ord-2690e096c09541e2a352479b05e1cb9b
Source dataset
uspto-grants-2006_08
Patent number
US07091212B2

Linked notes

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