tert-butyl 4-(2-methoxy-5-nitrophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate → 1-Piperidinecarboxylic acid, 4-(5-amino-2-methoxyphenyl)-, 1,1-dimethylethyl ester

HRID 1269143노트

반응식

HRID 1269143 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[C:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=1.[H][H]>CO.CCOC(C)=O.[Pd]>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][CH2:13]2)[CH:5]=1

참가 물질

5

반응물 2

HCID 18446884tert-butyl 4-(2-methoxy-5-nitrophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 184468851-Piperidinecarboxylic acid, 4-(5-amino-2-methoxyphenyl)-, 1,1-dimethylethyl ester수율 84%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 21584119Ethylacetate methanol용매

실험 절차

A solution of tert-butyl 4-(2-methoxy-5-nitrophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (1.30 g, 3.90 mmol) and 10% Pd/C (200.0 mg) in MeOH:EtOAc (1:4, 100 mL) was hydrogenated at room temperature for 72 h using the hydrogen balloon method. The reaction mixture was filtered through Celite and washed with ethanol (3×100 mL). The combined organic filtrates were concentrated in vacuo to afford tert-butyl 4-[5-amino-2-methoxyphenyl]-1-piperidinecarboxylate (1.00 g, 84%): ESMS m/e: 307.2 (M+H)+.

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with ethanol (3×100 mL)
  3. concentrationThe combined organic filtrates were concentrated in vacuo

출처 및 근거

ORD 기록
ord-75467ac318464022b7ce042e5ca52b7e
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199135B2

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