Diethyl Ether → Benzyl 4-tert-butoxycarbonyl-1-(3,4-dichlorobenzyl)cyclopenta[b]pyrrole-2-carboxylate

HRID 1596538

반응식

HRID 1596538 반응식
[N+](=[C:3]1[CH2:11][CH2:10][C:9]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=3)[C:7]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])=[CH:6][C:5]=2[C:4]1=[O:31])=[N-].[C:32]([OH:36])([CH3:35])([CH3:34])[CH3:33].C(OCC)C>N1C(C)=CC(C)=CC=1C>[C:32]([O:36][C:4]([C:3]1[C:5]2[C:9]([N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=3)[CH:7]([C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:22])[CH:6]=2)=[CH:10][CH:11]=1)=[O:31])([CH3:35])([CH3:34])[CH3:33]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 6386tert-ButanolHCID 21702187Benzyl 5-diazo-1-(3,4-dichlorobenzyl)-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylate

생성물 1

HCID 21702180Benzyl 4-tert-butoxycarbonyl-1-(3,4-dichlorobenzyl)cyclopenta[b]pyrrole-2-carboxylate수율 97%

시약·촉매·용매 1

HCID 79532,4,6-Trimethylpyridine용매

실험 절차

Benzyl 5-diazo-1-(3,4-dichlorobenzyl)-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylate (0.3 g) and t-butanol (1 mL) were heated at 180° C. in collidine (10 mL) for 30 minutes, cooled to room temperature, and poured into diethyl ether. The organic layer was washed with 2M HCl (100 mL), dried (MgSO4), and concentrated in vacuo to afford the title compound as an orange oil (0.32 g, 97%), NMR d(CDCl3) 1.45 (9H, s), 2.45-2.80 (4H, m), 3.78 (1H, dd), 5.20 (2H, d), 5.40 (2H, d), 6.80 (1H, dd), 6.95 (1H, s), 7.10 (1H, s), 7.30 (6H, m); M/z (+) 502, 500 (M+).

후처리

  1. washThe organic layer was washed with 2M HCl (100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-254d5c4a3d5c481990917d09a166ca3c
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06291507B1

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