Aluminium lithium hydride → HCID 21706309, compound

HRID 1595054Notes

Reaction equation

HRID 1595054 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([OH:12])(=[O:11])[C:8]([OH:10])=[O:9].[CH3:13][O:14][C:15]1[CH:52]=[CH:51][C:18]2[S:19][C:20]([C:37]3[CH:50]=[CH:49][C:40]([O:41][CH2:42][CH2:43][CH2:44][C:45](OC)=[O:46])=[CH:39][CH:38]=3)=[C:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[C:25]([O:35][CH3:36])[CH:24]=3)[C:17]=2[CH:16]=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C1COCC1.C(Cl)Cl.C([O-])(=O)C([O-])=O>[C:7]([OH:12])(=[O:11])[C:8]([OH:10])=[O:9].[CH3:13][O:14][C:15]1[CH:52]=[CH:51][C:18]2[S:19][C:20]([C:37]3[CH:38]=[CH:39][C:40]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][OH:46])=[CH:49][CH:50]=3)=[C:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[C:25]([O:35][CH3:36])[CH:24]=3)[C:17]=2[CH:16]=1

Participants

7

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21706358HCID 21706358, compoundHCID 131722655TFA triethylsilane

Product 1

HCID 21706309HCID 21706309, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 71081OxalateSolvent

Procedure

The title compound was prepared in 27% yield in three steps from LAH reduction of methyl 4-[4-[5-methoxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzoyl]benzo[b]thiophen-2-yl]phenoxy]butyrate (Part C of Example 38) in THF at 0-10° C. for 1 h, followed by dehydroxylation with Et3SiH/TFA in CH2Cl2 and oxalate formation as previously described.

Sources & evidence

ORD record
ord-b3418baeee6548dbbee8794f8405054a
Source dataset
uspto-grants-2001_09
Patent number
US06284756B1

Reaction notes

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