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Acetic Anhydride → HCID 90419021、化合物

HRID 514865
ノート
印刷プレビュー

反応式

HRID 514865 の反応式
[CH2:1]([C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].CN(C1C=CC=CN=1)C.[C:27](OC(=O)C)(=[O:29])[CH3:28].C(N(CC)CC)C>ClCCl>[C:27]([O:17][C:4]1([CH2:1][CH:2]=[CH2:3])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=[O:29])[CH3:28]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 21955339Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 90419021HCID 90419021、化合物収率 82.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

反応条件

温度
20 °C

実験手順

A solution of tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate (3.7 g, 14.51 mmol) in dichloromethane (20 mL) was treated with dimethylaminopyridine (1.8 g, 14.51 mmol), acetic anhydride (4.1 mL, 43.53 mmol) and triethylamine (6.1 mL, 43.53 mmol), and was stirred overnight at 20° C. The solvent was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. Combined organic extracts were washed with water, dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure, and purified by a standard method to provide the title compound 44B (3.4 g). LC-MS: m/z 284.4 (M+H)+

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washCombined organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. custompurified by a standard method

出典と根拠

ORDレコード
ord-0c6d5ea03c814fc5a27b8839d9fbb9ed
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09108921B2

反応ノート

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