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

HRID 1596538

Reaction equation

HRID 1596538 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-254d5c4a3d5c481990917d09a166ca3c
Source dataset
uspto-grants-2001_09
Patent number
US06291507B1

Linked notes

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