Hydrochloric Acid → 1-Benzyl-4-(2-benzyloxyphenyl)-4-piperidinol

HRID 238273ノート

反応式

HRID 238273 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Mg]Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 178419625HCID 178419625、化合物

生成物 1

HCID 118248891-Benzyl-4-(2-benzyloxyphenyl)-4-piperidinol収率 61.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1-benzyl-4-piperidone (0.5 g, 2.6 mmol) in THF (10 mL) was cooled to −78° C. and 2-(benzyloxy)phenyl magnesium bromide (3.2 mmol) was added. The mixture was stirred for 0.5 hours then allowed to warm to room temperature. Hydrochloric acid (1 N, 10 mL) was added carefully and the mixture stirred for 0.1 hour before adding a solution of aqueous sodium hydroxide (1 N, 30 mL). The products were extracted into ethyl acetate, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 0-50% ethyl acetate/hexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.6 g) as a clear, colourless oil.

後処理

  1. stirringthe mixture stirred for 0.1 hour
  2. extractionThe products were extracted into ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed by evaporation under vacuum
  6. customThe residue was purified by flash chromatography on silica eluting with 0-50% ethyl acetate/hexane
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

出典と根拠

ORDレコード
ord-31c37b59aeb44b2cb67d4ad3f71418fd
出典データセット
uspto-grants-2014_02
特許番号
US08642621B2

反応ノート

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