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

HRID 1441680ノート

反応式

HRID 1441680 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-16b619f70a0d4189b576a82578d32524
出典データセット
uspto-grants-2010_02
特許番号
US07655670B2

反応ノート

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