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

HRID 516402ノート

反応式

HRID 516402 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-e2f3c95e3bda489c8d0e045f55ba22f7
出典データセット
uspto-grants-2015_08
特許番号
US09108980B2

反応ノート

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