HCID 18707044, compound → HCID 18706950, compound

HRID 1422117Notes

Reaction equation

HRID 1422117 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]3=[C:20]([C:39]([O:41][CH3:42])=[O:40])[C:21]([C:35]([O:37][CH3:38])=[O:36])=[C:22]4[CH:23]=[CH:24][C:25]([CH2:26][O:27][Si](C(C)(C)C)(C)C)=[C:17]([N:18]34)[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.S(=O)(=O)(O)O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:19]3=[C:20]([C:39]([O:41][CH3:42])=[O:40])[C:21]([C:35]([O:37][CH3:38])=[O:36])=[C:22]4[CH:23]=[CH:24][C:25]([CH2:26][OH:27])=[C:17]([N:18]34)[CH:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 18707044HCID 18707044, compound2×

Product 1

HCID 18706950HCID 18706950, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

The general synthetic pathway outlined in example 89, step 5, and example 91 have been applied to proper starting material in the preparation of dimethyl 3-(4-benzyloxyphenyl)-5-(tert-butyldimethylsilanyloxymethyl)pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate. Dimethyl 3-(4-benzyloxyphenyl)-5-(tert-butyldimethylsilanyloxymethyl)pyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate (4.5 g, 7.7 mmol) was dissolved in 100 ml of methanol and 4 drops of sulfuric acid. The mixture was refluxed for 2 minutes, and cooled to room temperature. The yellow precipitate was filtered off to afford 3.24 g (89%) of dimethyl 3-(4benzyloxyphenyl)-5-hydroxymethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate as yellow crystals. 1H-NMR (CDCl3, 300 MHz) δ: 3.93 (s, 3H); 3.97 (s, 3H); 5.12 (s, 2H); 5.20 (s, 2H); 7.03 (d, 2H); 7.31-7.50 (m, 6H); 7.62 (m, 2H); 7.72 (m, 1H); 8.07 (m, 1H).

Workup

  1. temperatureThe mixture was refluxed for 2 minutes
  2. filtrationThe yellow precipitate was filtered off

Sources & evidence

ORD record
ord-09312fc0fba24ed89eb8c3f6ff203b5c
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

Loading…