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Tert-butyl 4-hydroxypiperidine-1-carboxylate → 1,1-Dimethylethyl 4-[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]oxy]-1-piperidinecarboxylate

HRID 362785
ノート
印刷プレビュー

反応式

HRID 362785 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[NH2:15][C:16]1[C:21]2[CH2:22][CH2:23][O:24][C:20]=2[C:19]([C:25](Cl)=[O:26])=[CH:18][C:17]=1[Cl:28]>CN(C)C1C=CN=CC=1.ClCCl>[NH2:15][C:16]1[C:21]2[CH2:22][CH2:23][O:24][C:20]=2[C:19]([C:25]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[O:26])=[CH:18][C:17]=1[Cl:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 539800704-Amino-5-chloro-2,3-dihydro-7-benzofurancarbonyl chloride

生成物 1

HCID 543178411,1-Dimethylethyl 4-[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]oxy]-1-piperidinecarboxylate収率 59.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344
Dichloromethane
溶媒
2 回

実験手順

A solution of 1,1-dimethylethyl 4-hydroxy-1-piperidinecarboxylate (4.02 g) and N,N-dimethyl-4-pyridinamine (3.7 g) in dichloromethane (200 ml) was stirred at room temperature. A solution of intermediate (7) (4.8 g) in CH2Cl2 (200 ml) was poured into the solution. The reaction mixture was stirred for 3 hours at room temperature. The mixture was washed with water, a 5% NaOH solution and again water. The organic layer was separated, dried over MgSO4, filtered and the solvent was evaporated. The residue (7.4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2). The pure fractions were collected and the solvent was evaporated, yielding 4.7 g of 1,1-dimethylethyl 4-[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]oxy]-1-piperidinecarboxylate (59%) (intermediate 8).

後処理

  1. washThe mixture was washed with water
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue (7.4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-93e9d805ef41497bb90b16380ca33c64
出典データセット
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05872131

反応ノート

読み込み中…

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