Hydrochloric Acid → (+/-)-3-(6-chloro-4-hydroxy-2,3-dihydro-1H-inden-5-yl)-2-hydroxypropyl 4-methylbenzenesulfonate

HRID 13948Notes

Reaction equation

HRID 13948 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]([OH:33])[CH2:14][C:15]2[C:16]([O:25]CC3C=CC=CC=3)=[C:17]3[C:21](=[CH:22][C:23]=2[Cl:24])[CH2:20][CH2:19][CH2:18]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl>[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]([OH:33])[CH2:14][C:15]2[C:16]([OH:25])=[C:17]3[C:21](=[CH:22][C:23]=2[Cl:24])[CH2:20][CH2:19][CH2:18]3)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86598558(+/-)-3-[4-(benzyloxy)-6-chloro-2,3-dihydro-1H-inden-5-yl]-2-hydroxypropyl 4-methylbenzenesulfonate

Product 1

HCID 86598559(+/-)-3-(6-chloro-4-hydroxy-2,3-dihydro-1H-inden-5-yl)-2-hydroxypropyl 4-methylbenzenesulfonateYield 91.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-3-[4-(benzyloxy)-6-chloro-2,3-dihydro-1H-inden-5-yl]-2-hydroxypropyl 4-methylbenzenesulfonate (6.30 g, 0.013 mol) with palladium on carbon (5 wt. %, 0.51 g) and hydrogen chloride (3.4 mL, 4 M in isopropanol) generally according to the procedure described for Intermediate 4 afforded 4.7 g (91%) of (±)-3-(6-chloro-4-hydroxy-2,3-dihydro-1H-inden-5-yl)-2-hydroxypropyl 4-methylbenzenesulfonate as a light yellow solid. mp 125-127° C.; Anal. calcd. for C19H21ClO5S.0.1H2O: C, 57.24; H, 5.36. Found: C, 56.92; H, 5.23.

Sources & evidence

ORD record
ord-448b2489a56d487896a51c1bc185de6d
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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