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

HRID 1366658ノート

反応式

HRID 1366658 の反応式
[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

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 15650612HCID 15650612、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0db471a3acb744eb8e837a7df0797d83
出典データセット
uspto-grants-2011_02
特許番号
US07893056B2

反応ノート

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