1-(4-Chlorobenzoyl)piperazine → 3-[4-(4-Chloro-benzoyl)-piperazin-1-yl]4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1361485

반응식

HRID 1361485 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[CH:10]([O:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])=[CH:17][CH:16]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([OH:11])[CH:12]([N:26]2[CH2:25][CH2:24][N:23]([C:21](=[O:22])[C:18]3[CH:17]=[CH:16][C:15]([Cl:14])=[CH:20][CH:19]=3)[CH2:28][CH2:27]2)[CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

3

반응물 2

HCID 41014841-(4-Chlorobenzoyl)piperazineHCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

생성물 1

HCID 669686813-[4-(4-Chloro-benzoyl)-piperazin-1-yl]4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester수율 84.2%

반응 조건

온도
130 °C

실험 절차

This is an example of Procedure A in Scheme 1 above. 6-Oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (1.85 g 1 eq) and (4-Chloro-phenyl)-piperazin-1-yl-methanone (2.2 g 1 eq) were added into a sealed tube. The mixture was heated to 130° C. for 5 h. The resulting oil was purified by column chromatography (EtOAc:MeOH:Et3N 10:1:0.01) to give 3.38 g of desired product as a sticky oil (84% yield). 1H-NMR (300 MHz, DMSO): δ 1.43 (s, 9 H), 2.40-2.80 (m, 4H), 3.15-3.85 (m, 9 H), 4.26-4.30 (m, 1 H), 7.35 (d, 2 H), 7.38 (d, 2 H) Retention Time (LC, method: Formic acid polar): 1.19 min. MS (M+H+): 410

후처리

  1. customThe resulting oil was purified by column chromatography (EtOAc:MeOH:Et3N 10:1:0.01)

출처 및 근거

ORD 기록
ord-459aaeabc7d640ffa11df11f69a6d515
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07880002B2

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