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

HRID 1689905노트

반응식

HRID 1689905 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-55bb470e73f64edcbc77102906cd6cae
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153629B2

반응 노트

불러오는 중…