Benzylamine → Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate

HRID 1193050노트

반응식

HRID 1193050 반응식
C(OC([C:6]1[CH2:7][CH2:8][N:9]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:10][C:11]=1[NH:12][CH2:13]C1C=CC=CC=1)=O)C.C(OC(C1CCN(C(OC(C)(C)C)=O)CC1=O)=O)C.C(N)C1C=CC=CC=1>C1(C)C=CC=CC=1>[C:23]([O:22][C:20]([N:9]1[CH2:8][CH2:7][CH:6]2[CH:11]([NH:12][CH2:13]2)[CH2:10]1)=[O:21])([CH3:24])([CH3:25])[CH3:26]

참가 물질

5

반응물 3

HCID 7504BenzylamineHCID 158529891-tert-Butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylateHCID 670868445-Benzylamino-3,6-dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

생성물 1

HCID 43810891Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate수율 92.5%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

5-Benzylamino-3,6-dihydro-2H-pyridine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester. 3-Oxo-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (8.15 g, 30 mmol) from Step A and benzyl amine (3.43 g, 31.8 mmol) were dissolved into toluene (150 mL). The mixture was refluxed vigorously for 72 h and the generated water was collected into Dean-Stark apparatus. The residual solution was concentrated to yield the title compound (10.2 g, 92.5%). MS (ESI) mass calcd. for C20H28N2O4, 360.45, m/z found, 361.2 [M+H]+. The crude product was carried to the next step without any purification.

후처리

  1. temperatureThe mixture was refluxed vigorously for 72 h
  2. customthe generated water was collected into Dean-Stark apparatus
  3. concentrationThe residual solution was concentrated

출처 및 근거

ORD 기록
ord-6fa24ab004ab48ee8583b39545ae58ef
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680275B2

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