Acetic Acid → 1-(Methylcarbonyloxy-methyl)-5-(4-t-butyl-cyclohexyl-methyl)-spiro[indoline-3,4'-piperidin]-2-one

HRID 1441677

Reaction equation

HRID 1441677 reaction equation
COC([CH2:5][N:6]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]2([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[C:7]1=[O:20])=O.[C:21]([CH:25]1[CH2:30][CH2:29][CH:28]([CH:31]=O)[CH2:27][CH2:26]1)([CH3:24])([CH3:23])[CH3:22].[C:33]([OH:36])(=[O:35])[CH3:34].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:34][C:33]([O:36][CH2:5][N:6]1[C:19]2[C:14](=[CH:15][C:16]([CH2:31][CH:28]3[CH2:27][CH2:26][CH:25]([C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:30][CH2:29]3)=[CH:17][CH:18]=2)[C:8]2([CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[C:7]1=[O:20])=[O:35]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 88655Cyclohexanecarboxaldehyde, 4-(1,1-dimethylethyl)-HCID 5049666Sodium triacetoxyborohydrideHCID 591645371-(Methoxycarbonylmethyl)-spiro[indoline-3,4'-piperidin]-2-one

Product 1

HCID 685423601-(Methylcarbonyloxy-methyl)-5-(4-t-butyl-cyclohexyl-methyl)-spiro[indoline-3,4'-piperidin]-2-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-(Methoxycarbonyl-methyl)-spiro[indoline-3,4′-piperidin]-2-one (0.0137 g, 0.049 mmol) and 4-tert-butyl-cyclohexanecarbaldehyde (0.01 g, 0.06 mmol) were dissolved in dry 1,2-dichloroethane (1.5 mL). To the reaction mixture was then added glacial acetic acid (0.003 g, 0.049 mmol) under nitrogen atmosphere and the reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was then added, at room temperature, sodium triacetoxyborohydride (0.018 g, 0.084 mmol) under nitrogen atmosphere and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was then partitioned with aqueous NaHCO3 and dichloromethane. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (4.5% ammonia 2.0 M in methanol/dichloromethane) to yield the title compound as an oil.

Workup

  1. additionTo the reaction mixture was then added, at room temperature
  2. customThe reaction mixture was then partitioned with aqueous NaHCO3 and dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customto yield a crude oil
  8. customThe crude oil was purified via flash chromatography (4.5% ammonia 2.0 M in methanol/dichloromethane)

Sources & evidence

ORD record
ord-9bdd9ad7531a482f8c6d307dfa0e4014
Source dataset
uspto-grants-2010_02
Patent number
US07655670B2

Linked notes

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