Acetic Acid → tert-butyl 4-allyl-4-((1-tosyl-1H-indol-3-yl)methylamino)piperidine-1-carboxylate

HRID 41567

反応式

HRID 41567 の反応式
[S:1]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20]=O)=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:22]([C:25]1([NH2:38])[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1)[CH:23]=[CH2:24].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[CH2:22]([C:25]1([NH:38][CH2:20][C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]([S:1]([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=3)(=[O:3])=[O:2])[CH:12]=2)[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1)[CH:23]=[CH2:24]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 7358171-(4-Methylbenzene-1-sulfonyl)-1H-indole-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67287394741687-08-1

生成物 1

HCID 67252781tert-butyl 4-allyl-4-((1-tosyl-1H-indol-3-yl)methylamino)piperidine-1-carboxylate収率 60.1%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
60 °C

実験手順

To a solution of 1-tosyl-1H-indole-3-carbaldehyde [50562-79-3] (1.90 g, 6.35 mmol) in 1,2-dichloroethane (30 mL) were added tert-butyl 4-allyl-4-aminopiperidine-1-carboxylate [741687-08-1] (1.52 g, 6.35 mmol) and acetic acid (381 mg, 6.35 mmol). The resulting solution was heated at 60° C. for 3 h. Then NaBH(OAc)3 was added and the reaction mixture was heated at 60° C. for 38 h. The mixture was cooled to rt, saturated NaHCO3 solution (30 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with water and brine, then dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude mixture was purified by flash-column chromatography over silicagel (eluent: 20% ethyl acetate/hexane) to yield the title compound (2.0 g, 60%). [LCMS RtE=0.34 min, [M+H]+=524.0]

後処理

  1. temperaturethe reaction mixture was heated at 60° C. for 38 h
  2. temperatureThe mixture was cooled to rt
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude mixture was purified by flash-column chromatography over silicagel (eluent: 20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-f507aec85ad84e9ca7dc89d2e278bfa1
出典データセット
uspto-grants-2013_09
特許番号
US08530648B2

関連ノート

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