Acetic Acid → (R)-3-[2-((S)-1-Aminoethyl)benzoimidazol-1-yl]piperidine-1-carboxylic acid tertbutyl ester

HRID 242821노트

반응식

HRID 242821 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[C@@H:23]([NH:25]C(OCC2C=CC=CC=2)=O)[CH3:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(O)=O>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[C@@H:23]([NH2:25])[CH3:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 68157686(R)-3-[2-((S)-1-Benzyloxycarbonylaminoethyl)benzoimidazol-1-yl]piperidine-1-carboxylic acid tertbutyl ester

생성물 1

HCID 68157746(R)-3-[2-((S)-1-Aminoethyl)benzoimidazol-1-yl]piperidine-1-carboxylic acid tertbutyl ester수율 83.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture of (R)-3-[2-((S)-1-benzyloxycarbonylaminoethyl)benzoimidazol-1-yl]piperidine-1-carboxylic acid tertbutyl ester (2.75 g, 5.75 mmol) 10% Pd/C (275 mg) and AcOH (4 mL) in EtOAc (40 mL) was purged with a stream of nitrogen and then was stirred at RT for 20 h under an hydrogen atmosphere. The suspension was then filtered through a PTFE frit and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) affording (R)-3-[2-((S)-1-Aminoethyl)benzoimidazol-1-yl]piperidine-1-carboxylic acid tertbutyl ester as a white foam (1.65 g, 83%). LCMS: RT 2.30 min [M+H-tBu]+ 289.2.

후처리

  1. customwas purged with a stream of nitrogen
  2. filtrationThe suspension was then filtered through a PTFE frit
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)

출처 및 근거

ORD 기록
ord-01c472b399234ac39febd8ee9dbefd75
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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