ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

tert-Butyl 4-formylpiperidine-1-carboxylate → (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]amine

HRID 429824
ノート
印刷プレビュー

反応式

HRID 429824 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([NH:13][CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH:29]=O)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:29][CH:26]3[CH2:27][CH2:28][N:23]([C:21]([O:20][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:22])[CH2:24][CH2:25]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1
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 3

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 11106515(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamine

生成物 1

HCID 54410775(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]amine収率 82%

試薬・触媒・溶媒 1

HCID 6365
1,1-Dichloroethane
溶媒

実験手順

To a solution of (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamine (2.38 grams, 11.6 mmol) and 1-(tert-butoxycarbonyl)piperidine-4-carboxaldehyde (2.47 grams, 11.6 mmol) in dichloroethane (20 ml) was added sodium triacetoxyborohydride (3.67 grams,17.4 mmole). The reaction mixture was stirred for 16 hours at room temperature. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was washed with water, dried over potassium carbonate and concentrated under reduced pressure to leave a residue, which was purified by flash chromatography on silica gel using 30% ethyl acetate in hexane. Appropriate fractions were combined and concentrated to give (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]amine as a oil (3.78 g, 82%), M+H 403.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane and saturated sodium bicarbonate solution
  3. washThe organic layer was washed with water
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated under reduced pressure
  6. customto leave a residue, which
  7. customwas purified by flash chromatography on silica gel using 30% ethyl acetate in hexane
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-a91d7d497a014bb0ad40f5ff789587b3
出典データセット
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06319920B1

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート