HCID 18707009, compound → HCID 18707012, compound

HRID 1422121Notes

Reaction equation

[CH2:1]([C:3]1[C:4]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[C:5]2[N:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=13)[C:7]([C:14](OC)=[O:15])=[CH:6]2)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:1]([C:3]1[C:12]2[N:13]3[C:8](=[C:7]([CH2:14][OH:15])[CH:6]=[C:5]3[C:4]=1[C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[CH:9]=[CH:10][CH:11]=2)[CH3:2]

Participants

Reactant 2

HCID 18707009HCID 18707009, compound

HCID 21226445Aluminium lithium hydride

Product 1

HCID 18707012HCID 18707012, compoundYield 83%

Procedure

The general synthetic pathway outlined in example 1 have been applied to proper starting materials in the preparation of methyl 4-ethyl-3-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine-1-carboxylate, which was reacted with lithium aluminium hydride by the general synthetic principle outlined in example 1, step 4, to afford 1-ethyl-4-hydroxymethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine as yellow crystals in 83% yield. MS(SP): m/z 305 (M+). 1H-NMR (CDCl3, 200 MHz) δ: 1.47 (t, 3H); 3.24 (q, 2H); 3.90 (s, 3H); 5.18 (s, 2H); 7.09 (d, 2H); 7.57 (s, 1H); 7.65 (dd, 1H); 7.73 (d, 2H); 7.92 (d, 1H); 8.01 (d, 1H).

Sources & evidence

ORD record: ord-c090ab1ce21a41249f58878980460cb0
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080754

Reaction notes

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