Acetic Acid → HCID 18941020, compound

HRID 356123Notes

Reaction equation

HRID 356123 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([C:6]2[S:7][C:8]3[CH2:17][C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:9]=3[N:10]=2)[CH2:2]1.[C:18](O)(=O)[CH3:19].[C:22](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.CC(C)=O>[CH:18]([N:1]1[CH2:5][CH2:4][CH:3]([C:6]2[S:7][C:8]3[CH2:17][C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:9]=3[N:10]=2)[CH2:2]1)([CH3:19])[CH3:22]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 9859629HCID 9859629, compound

Product 1

HCID 18941020HCID 18941020, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 75 mg of 2-(3-pyrrolidinyl)-8H-indeno[1,2-d]thiazole in 1.4 ml of methylene chloride, were added 0.18 ml of acetic acid, 0.045 ml of acetone, and 147 mg of sodium triacetoxyborohydride, followed by stirring at room temperature for 2 hours. Water and a saturated aqueous solution of sodium bicarbonate were added to the reaction mixture. The resulting mixture was extracted with chloroform, followed by drying over anhydrous magnesium sulfate. The solvent was then evaporated and the resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol:29% ammonium=300:10:1), whereby 30 mg of 2-(1-isopropyl-3-pyrrolidinyl)-8H-indeno[1,2-d]thiazole was obtained. The resulting product was dissolved in methanol. Fumaric acid was added to cause crystallization, and crystals were recrystallized from acetonitrile-methanol to give a fumarate.

Workup

  1. extractionThe resulting mixture was extracted with chloroform
  2. dry with materialby drying over anhydrous magnesium sulfate
  3. customThe solvent was then evaporated
  4. customthe resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol:29% ammonium=300:10:1)

Sources & evidence

ORD record
ord-3b89ddde082f4a8dbc2e6b13f8b000c0
Source dataset
uspto-grants-1998_11
Patent number
US05834499

Reaction notes

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