Acetic Acid → 1-(Methylcarbonyloxy-methyl)-5-(2-decahydronaphthyl)-spiro[indoline-3,4'-piperidin]-2-one

HRID 1441680Notes

Reaction equation

HRID 1441680 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.[CH2:21]1[CH:30]2[CH:25]([CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:24][CH2:23][C:22]1=O.[C:32]([OH:35])(=[O:34])[CH3:33].C([BH3-])#N>C1COCC1.ClCCCl>[CH3:33][C:32]([O:35][CH2:5][N:6]1[C:19]2[C:14](=[CH:15][C:16]([CH:22]3[CH2:23][CH2:24][CH:25]4[CH:30]([CH2:29][CH2:28][CH2:27][CH2:26]4)[CH2:21]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:34]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1003282-DecaloneHCID 498716Cyano-borohydrideHCID 591645371-(Methoxycarbonylmethyl)-spiro[indoline-3,4'-piperidin]-2-one

Product 1

HCID 685396681-(Methylcarbonyloxy-methyl)-5-(2-decahydronaphthyl)-spiro[indoline-3,4'-piperidin]-2-one

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(Methoxycarbonylmethyl)-spiro[indoline-3,4′-piperidin]-2-one (0.013 g, 0.049 mmol) was dissolved in dry THF (1.0 mL) and dry 1,2-dichloroethane (0.3 mL). Octahydro-naphthalen-2-one (0.008 g, 0.054 mmol), glacial acetic acid (0.003 g, 0.049 mmol), MP-cyanoborohydride (Polymer support from Argonaut) (0.043 g, 0.099 mmol) were added and the reaction mixture was stirred at room temperature for 18 hrs. The mixture was then filtered, the resin washed with dichloromethane and the solvent evaporated in vacuo to yield the crude compound. The crude compound was purified via flash chromatography (5% methanol/dichloromethane) to yield the title compound as a foam.

Workup

  1. filtrationThe mixture was then filtered
  2. washthe resin washed with dichloromethane
  3. customthe solvent evaporated in vacuo
  4. customto yield the crude compound
  5. customThe crude compound was purified via flash chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-16b619f70a0d4189b576a82578d32524
Source dataset
uspto-grants-2010_02
Patent number
US07655670B2

Reaction notes

Loading…