Triethylamine → Tert-butyl 3-(methylcarbamoyl)piperidine-1-carboxylate

HRID 1689905ノート

反応式

HRID 1689905 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17](N1C=CN=C1)([N:19]1C=CN=C1)=O.C(N(CC)CC)C.Cl.CN>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=[O:16])[NH:19][CH3:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 6364545Methylamine hydrochloride

生成物 1

HCID 18154653Tert-butyl 3-(methylcarbamoyl)piperidine-1-carboxylate収率 77.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Amine preparation: To a solution of 1-(tert-butoxycarbonyl)-3-piperidine-carboxylic acid (0.50 g) in DMF (3 mL) was added 1,1′-carbonyldiimidazole (0.70 g). The reaction mixture was stirred for 4 h and then triethylamine (0.60 mL) followed by methylamine hydrochloride (0.29 g) was added. After stirring for 24 h the reaction mixture was then diluted with ethyl acetate, washed with water, brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to yield 3-methylcarbamoyl-piperidine-1-carboxylic acid tert-butyl ester (0.41 g). Treatment of this compound with HCl in DCM/MeOH yielded the desired amine, which was isolated as the hydrochloride salt.

後処理

  1. additionwas added
  2. stirringAfter stirring for 24 h the reaction mixture
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-55bb470e73f64edcbc77102906cd6cae
出典データセット
uspto-grants-2012_04
特許番号
US08153629B2

反応ノート

読み込み中…