Dimethyl acetylenedicarboxylate → Dimethyl 3-(4-benzyloxyphenyl)-5-(tert-butyldimethylsilanyloxymethyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate
Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([CH2:33][CH3:34])=[C:17]3[N:22]([CH:23]=2)[CH:21]=[CH:20][CH:19]=[C:18]3[CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([C:41]([O:43][CH3:44])=[O:42])#[C:36][C:37]([O:39][CH3:40])=[O:38]>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3=[C:35]([C:41]([O:43][CH3:44])=[O:42])[C:36]([C:37]([O:39][CH3:40])=[O:38])=[C:21]4[CH:20]=[CH:19][C:18]([CH2:24][O:25][Si:26]([C:29]([CH3:30])([CH3:32])[CH3:31])([CH3:27])[CH3:28])=[C:17]([N:22]34)[C:16]=2[CH2:33][CH3:34])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
2-(4-Benzyloxyphenyl)-8-(tert-butyldimethylsilanyloxymethyl)-1-ethylindolizine, prepared in example 81, step 5, was reacted with dimethyl acetylene dicarboxylate by the general synthetic principle outlined in example 23, step 6, to afford dimethyl 3-(4-benzyloxyphenyl)-5-(tert-butyldimethylsilanyloxymethyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylate, which was hydrolysed and desilylated by the general synthetic principle outlined in example 23, step 7, to afford 3-(4-benzyloxyphenyl)-4-ethyl-5-hydroxymethylpyrrolo[2,1,5-cd]indolizine-1,2-dicarboxylic acid as yellow crystals in 70% yield. 1H--NMR (DMSO-d6, 200 MHz) δ: 1.32 (t, 3 H); 3.09 (q, 2 H); 5.18 (s, 2 H); 5.19 (s, 2 H); 7.19 (d, 2 H); 7.31-7.58 (m, 7 H); 8.08 (d, 1 H); 8.40 (d, 1 H).
Sources & evidence
- ORD record
- ord-8af29c4bd5aa4f75a9a2609ce326cf58
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06080754
Reaction notes
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