Triethylamine → Benzyl 3-(3-hydroxypropyl)piperidine-1-carboxylate

HRID 2038168ノート

反応式

HRID 2038168 の反応式
[C:1]1([CH2:7][O:8][C:9]([O:11]N2C(=O)CCC2=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([CH2:25][CH2:26][CH2:27][OH:28])[CH2:20]1.C(N(CC)CC)C>ClCCl>[OH:28][CH2:27][CH2:26][CH2:25][CH:21]1[CH2:22][CH2:23][CH2:24][N:19]([C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:11])[CH2:20]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 47124763-Piperidin-3-ylpropan-1-ol

生成物 1

HCID 58306111Benzyl 3-(3-hydroxypropyl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-({[(Phenylmethyl)oxy]carbonyl}oxy)-2,5-pyrrolidinedione (commercially available, for example, from Aldrich) (8.70 g, 34.9 mmol) was added portionwise to a stirred mixture of 3-(3-piperidinyl)-1-propanol (commercially available, for example, from Astatech) (5.02 g, 35 mmol) and triethylamine (5 mL, 3.63 g, 35.9 mmol) in dichloromethane (100 mL) at room temperature. The resultant mixture was allowed to stand at room temperature for 18 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (100 mL). The organic phase was dried (MgSO4), filtered and evaporated. The sample was purified by chromatography on silica (100 g cartridge loaded in dichloromethane) using a gradient of 0-100% ethyl acetate-cyclohexane over 40 minutes. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a colourless liquid (8.45 g).

後処理

  1. customat room temperature
  2. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (100 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe sample was purified by chromatography on silica (100 g cartridge loaded in dichloromethane)
  7. customover 40 minutes
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-a92a9731b99c4d77a7492ff2aa5f6338
出典データセット
uspto-grants-2013_11
特許番号
US08575340B2

反応ノート

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