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

HRID 1596538

反応式

HRID 1596538 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 79532,4,6-Trimethylpyridine溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-254d5c4a3d5c481990917d09a166ca3c
出典データセット
uspto-grants-2001_09
特許番号
US06291507B1

関連ノート

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