Triethylamine → 1,1-Dimethylethyl (2S)-4-[(4-amino-2-chlorophenyl)methyl]-2-methyl-1-piperazinecarboxylate

HRID 644753노트

반응식

HRID 644753 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:14]([CH3:25])[CH2:13]1.C(N(CC)CC)C>[Pt].CO.C(Cl)Cl>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C@@H:14]([CH3:25])[CH2:13]2)=[C:2]([Cl:1])[CH:7]=1

참가 물질

6

반응물 2

HCID 8471TriethylamineHCID 592621281,1-Dimethylethyl (2S)-4-[(2-chloro-4-nitrophenyl)methyl]-2-methyl-1-piperazinecarboxylate

생성물 1

HCID 592621321,1-Dimethylethyl (2S)-4-[(4-amino-2-chlorophenyl)methyl]-2-methyl-1-piperazinecarboxylate수율 68.4%

시약·촉매·용매 3

HCID 23939Platinum촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 1,1-dimethylethyl (2S)-4-[(2-chloro-4-nitrophenyl)methyl]-2-methyl-1-piperazinecarboxylate (D103) (0.199 g, 0.538 mmol), triethylamine (0.75 mL, 5.38 mmol) and 5% Pt/C catalyst (0.134 g) in MeOH (5 mL) was hydrogenated at room temperature and atmospheric pressure for 3 h. The catalyst was removed by filtration and the filtrate was concentrated to give a colourless oil which was dissolved in DCM. The DCM solution was washed with water (×2) and brine, then dried and concentrated to give the crude product. Purification by column chromatography eluting with 10-40% EtOAc/pentane gave the title compound as a colourless oil (0.125 g). δH (CDCl3, 400 MHz) 7.19 (1H, d), 6.69 (1H, d), 6.54 (1H, dd), 4.18 (1H, br.s), 3.79 (1H, d), 3.70 (2H, br.s), 3.45 (2H, m), 3.07 (1H, td), 2.74 (1H, m), 2.60 (1H, m), 2.19 (1H, dd), 2.03 (1H, m), 1.45 (9H, s), 1.22 (3H, d). MS (ES): MH+ 340/342.

후처리

  1. customwas hydrogenated at room temperature
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customto give a colourless oil which
  5. washThe DCM solution was washed with water (×2) and brine
  6. customdried
  7. concentrationconcentrated
  8. customto give the crude product
  9. customPurification by column chromatography
  10. washeluting with 10-40% EtOAc/pentane

출처 및 근거

ORD 기록
ord-2704d3de5b3542d9bc3f20c5a2d71d00
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700599B2

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