Toluene → HCID 67084515, compound

HRID 2103636Notes

Reaction equation

HRID 2103636 reaction equation
C([O:3][C:4](=O)/[C:5](/[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1)=[CH:6]/[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>>[CH:7]1(/[CH:6]=[C:5](\[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH2:21][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)(=[O:20])=[O:19])=[CH:14][CH:13]=2)/[CH2:4][OH:3])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 67084584HCID 67084584, compound

Product 1

HCID 67084515HCID 67084515, compoundYield 58%

Procedure

Following the method of example 54e, reduction of (E)-3-cyclopentyl-2-[4-(pyridin-3-ylmethanesulfonyl)-phenyl]-acrylic acid ethyl ester (2.43 g, 6.08 mmol) with DIBAL in toluene (12.61 mL, 15.2 mmol) gives the title compound as an amorphous solid (1.26 g).

Sources & evidence

ORD record
ord-e9bdd538acab4ba8b20eb58eb807ae9f
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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