Triethylamine → Benzyl octahydroquinoxaline-1(2H)-carboxylate

HRID 1366658노트

반응식

HRID 1366658 반응식
[NH:1]1[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>ClCCl>[N:1]1([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[NH:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 15650612HCID 15650612, 화합물

생성물 1

HCID 45358656Benzyl octahydroquinoxaline-1(2H)-carboxylate수율 85%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To (4aR,8aS)-decahydroquinoxaline (1.4 g, 10 mmol) in dichloromethane (50 mL) was added triethylamine (1.7 mL, 12 mmol) followed by dropwise benzyl chloroformate (1.71 g, 10 mmol). The reaction mixture was stirred at room temperature for 2 h before being diluted with dichloromethane and washed with 1N NaOH followed by sat. aq. NH4Cl. The combined organic layers were washed with brine, dried (MgSO4) and concentrated to provide the crude product, which was purified via Combiflash to yield phenylmethyl octahydro-1(2H)-quinoxalinecarboxylate (enantiomeric mixture, cis) (2.32 g, 85%). LCMS: (M+H)+: 275.1.

후처리

  1. washwashed with 1N NaOH
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto provide the crude product, which
  6. customwas purified via Combiflash

출처 및 근거

ORD 기록
ord-0db471a3acb744eb8e837a7df0797d83
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

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