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

HRID 1441680노트

반응식

HRID 1441680 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-16b619f70a0d4189b576a82578d32524
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655670B2

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