Diisopropylethylamine → 1,1-Dimethylethyl (2S)-4-[(2-chloro-4-nitrophenyl)methyl]-2-methyl-1-piperazinecarboxylate

HRID 534782

반응식

HRID 534782 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[Cl:12].Cl.[CH3:14][C@H:15]1[CH2:20][NH:19][CH2:18][CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[CH2:2][N:19]1[CH2:18][CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:15]([CH3:14])[CH2:20]1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 30163681-(Bromomethyl)-2-chloro-4-nitrobenzeneHCID 45072182(S)-tert-butyl 2-methylpiperazine-1-carboxylate hydrochloride

생성물 1

HCID 592621281,1-Dimethylethyl (2S)-4-[(2-chloro-4-nitrophenyl)methyl]-2-methyl-1-piperazinecarboxylate수율 34.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

A mixture of crude 1-(bromomethyl)-2-chloro-4-nitrobenzene (D102) (0.391 g), 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate hydrochloride (0.407 g, 1.72 mmol) and Hunig's base (0.625 mL, 3.59 mmol) in dry DMF (3 mL) was stirred at room temperature for 10 minutes. The reaction mixture was concentrated to give an orange oil which was dissolved in DCM and washed with water (×2) and brine, then dried and concentrated to give an orange oil. Purification by column chromatography eluting with 0-30% EtOAc/pentane gave the title compound as a yellow oil (0.199 g). δH (CDCl3, 400 MHz) 8.24 (1H, d), 8.12 (1H, dd), 7.77 (1H, d), 4.24 (1H, br.s), 3.85 (1H, d), 3.63 (2H, s), 3.14 (1H, td), 2.76 (1H, m), 2.59 (1H, m), 2.33 (1H, dd), 2.18 (1H, m), 1.47 (9H, s), 1.28 (3H, d). MS (ES): MH+ 370/372,

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customto give an orange oil which
  3. washwashed with water (×2) and brine
  4. customdried
  5. concentrationconcentrated
  6. customto give an orange oil
  7. customPurification by column chromatography
  8. washeluting with 0-30% EtOAc/pentane

출처 및 근거

ORD 기록
ord-92ef30901bb549da81580cf8c3595c75
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853218B2

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