Acetone → HCID 68503410, compound

HRID 1510025Notes

Reaction equation

HRID 1510025 reaction equation
[CH3:1][C:2]12[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:3]1[NH:4][CH2:5][CH2:6][CH2:7]2.[CH3:15][C:16]([CH3:18])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[CH:16]([N:4]1[CH2:5][CH2:6][CH2:7][C:2]2([CH3:1])[CH2:14][C:13]3[C:8]([CH:3]12)=[CH:9][CH:10]=[CH:11][CH:12]=3)([CH3:18])[CH3:15]

Participants

6

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 68495649HCID 68495649, compound

Product 1

HCID 68503410HCID 68503410, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (4aRS,9bRS)-4a-methyl-2,3,4,4a,5,9b-hexahydro-1H-indeno[1,2-b]pyridine (140 mg) and acetone (217 mg) in 1,2-dichloroethane was added sodium triacetoxyborohydride (792 mg), followed by stirring at room temperature for 3 days. A 1 M aqueous sodium hydroxide solution was added thereto, followed by extraction with chloroform, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure to obtain (4aRS,9bRS)-1-isopropyl-4a-methyl-2,3,4,4a,5,9b-hexahydro-1H-indeno[1,2-b]pyridine (138 mg) as an oily substance. This was made into a salt using an equivalent amount of methanesulfonic acid by a conventional method, washed with ethyl acetate, and collected by filtration to obtain (4aRS,9bRS)-1-isopropyl-4a-methyl-2,3,4,4a,5,9b-hexahydro-1H-indeno[1,2-b]pyridine methanesulfonate (95 mg) as a colorless powder.

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-e820f8f89d0a48bebaa33238b7914358
Source dataset
uspto-grants-2012_07
Patent number
US08211907B2

Reaction notes

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