Oxalate → HCID 22111301, compound

HRID 565434Notes

Reaction equation

HRID 565434 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:36]=[CH:37][C:38]=1[CH2:39][N:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1)[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:22]1[CH:35]=[CH:34][C:25]([O:26][CH2:27][CH2:28][CH2:29][C:30](OC)=[O:31])=[CH:24][CH:23]=1.[C:45]([O-:50])(=[O:49])[C:46]([O-:48])=[O:47]>C1COCC1>[C:45]([OH:50])(=[O:49])[C:46]([OH:48])=[O:47].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:36]=[CH:37][C:38]=1[CH2:39][N:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1)[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:22]1[CH:35]=[CH:34][C:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 71081OxalateHCID 15485945HCID 15485945, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22111301HCID 22111301, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared in 70% yield in two steps from LAH reduction of methyl 4-[4-[1-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]indol-2-yl]phenoxy]butyrate (free base of Example 8) in THF at 0° C. for 1 h, followed by oxalate formation as previously described.

Sources & evidence

ORD record
ord-5bedda535f8f414f844cf394051fcd84
Source dataset
uspto-grants-2001_01
Patent number
US06172100B2

Reaction notes

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