Potassium Hydroxide → 5-methyl-5-[(3S)-3-phenoxypyrrolidin-1-yl]-2,2-diphenylhexanamide

HRID 2387674ノート

反応式

HRID 2387674 の反応式
[OH-:1].[K+].[CH3:3][C:4]([N:23]1[CH2:27][CH2:26][C@H:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24]1)([CH3:22])[CH2:5][CH2:6][C:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:8]#[N:9]>CC(O)(CC)CC>[CH3:22][C:4]([N:23]1[CH2:27][CH2:26][C@H:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24]1)([CH3:3])[CH2:5][CH2:6][C:7]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:8]([NH2:9])=[O:1]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 547579545-Methyl-5-[(3S)-3-phenoxypyrrolidin-1-yl]-2,2-diphenylhexanenitrile

生成物 1

HCID 160651355-methyl-5-[(3S)-3-phenoxypyrrolidin-1-yl]-2,2-diphenylhexanamide収率 82%

試薬・触媒・溶媒 1

HCID 64933-methyl-3-Pentanol溶媒

実験手順

Potassium hydroxide (5.10 g, 91.98 mmol) was added to a solution of the product of example 1 (1.95 g, 4.60 mmol) in 3-methyl-3-pentanol (40 mL) and the mixture was heated under reflux for 24 hours. The reaction mixture was then cooled to room temperature, concentrated in vacuo and the residue was partitioned between ethyl acetate (70 mL) and water (40 mL). The aqueous layer was separated, extracted with ethyl acetate (50 mL) and the combined organic solution was dried over sodium sulfate and concentrated in vacuo. The residue was then re-crystallised from hexane/ethyl acetate and dried under vacuum for 18 hours to afford the title compound as a white solid in 82% yield, 1.66 g.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. concentrationconcentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate (70 mL) and water (40 mL)
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate (50 mL)
  7. dry with materialthe combined organic solution was dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was then re-crystallised from hexane/ethyl acetate
  10. customdried under vacuum for 18 hours

出典と根拠

ORDレコード
ord-1e0a9272cf494045840ccbaf329ce35a
出典データセット
uspto-grants-2012_09
特許番号
US08268881B2

反応ノート

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