Dimethylamine → Benzyl 4-[(dimethylamino)sulfonyl]-1-piperidinecarboxylate

HRID 1256561ノート

反応式

HRID 1256561 の反応式
Cl[S:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)(=[O:4])=[O:3].[CH3:21][NH:22][CH3:23]>C1COCC1>[CH3:21][N:22]([CH3:23])[S:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)(=[O:4])=[O:3]

参加物

4

反応物 2

HCID 674DimethylamineHCID 21931260Benzyl 4-(chlorosulfonyl)piperidine-1-carboxylate

生成物 1

HCID 53587548Benzyl 4-[(dimethylamino)sulfonyl]-1-piperidinecarboxylate収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 190 mg (0.6 mmol) of benzyl 4-(chlorosulfonyl)-1-piperidinecarboxylate in 10 mL THF was treated with a 10-fold excess of 40% aq. dimethylamine and the mixture was stirred at room temperature for 2 hrs. The THF was removed under vacuum. The residue was diluted with water, extracted with CH2Cl2, and dried. Chromatography on alumina, eluting with CH2Cl2, gave 175 mg (89% yield) of benzyl 4-[(dimethylamino)sulfonyl]-1-piperidinecarboxylate as an oil: 1H NMR (CDCl3) δ 7.40-7.30 (m, 5H), 5.13 (s, 2H), 4.31 (m, 2H), 3.10 (tt, J=12.0, 3.7 Hz, 1H), 2.92 (s, 6H), 2.85-2.75 (m, 2H), 2.04 (br d, J=13.7 Hz, 2H), 1.76 (dq, J=12.6, 4.5 Hz, 2H).

後処理

  1. customThe THF was removed under vacuum
  2. additionThe residue was diluted with water
  3. extractionextracted with CH2Cl2
  4. customdried
  5. washChromatography on alumina, eluting with CH2Cl2

出典と根拠

ORDレコード
ord-bb223dbb23aa4451b1cde1851d7eb72d
出典データセット
uspto-grants-2013_06
特許番号
US08461158B2

反応ノート

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