Acetic Acid → HCID 68537233, compound

HRID 1441672Notes

Reaction equation

HRID 1441672 reaction equation
[CH3:1][C:2]([O:4][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:3].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][C:2]([O:4][CH2:5][N:6]1[C:19]2[C:14](=[CH:15][C:16]([CH2:26][C:25]3[CH:28]=[CH:29][C:22]([Cl:21])=[CH:23][CH:24]=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:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68544470HCID 68544470, compound

Product 1

HCID 68537233HCID 68537233, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-(Methylcarbonyloxy-methyl)-spiro[indoline-3,4′-piperidin]-2-one (0.026 g, 0.095 mmol) and 4-chloro-benzaldehyde (0.02 g, 0.14 mmol) were dissolved in dry 1,2-dichloroethane (1.5 mL). To the reaction mixture was then added glacial acetic acid (0.006 g, 0.095 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 (0.034 g, 0.16 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 (2.5% methanol/dichloromethane) to yield the title compound as a solid.

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 (2.5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-49b5671196b743f9be05d44598b1db5b
Source dataset
uspto-grants-2010_02
Patent number
US07655670B2

Reaction notes

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