(+/-)-3-[5-(Benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl]-2-hydroxypropyl 4-methylbenzenesulfonate → (+/-)-2-Hydroxy-3-(5-hydroxy-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl)propyl 4-methylbenzenesulfonate

HRID 13937Notes

Reaction equation

HRID 13937 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]([OH:37])[CH2:14][C:15]2[C:16]([O:29]CC3C=CC=CC=3)=[C:17]3[C:22](=[C:23]([O:25][CH3:26])[CH:24]=2)[CH:21]2[CH2:27][CH2:28][CH:18]3[CH2:19][CH2:20]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]([OH:37])[CH2:14][C:15]2[C:16]([OH:29])=[C:17]3[C:22](=[C:23]([O:25][CH3:26])[CH:24]=2)[CH:21]2[CH2:20][CH2:19][CH:18]3[CH2:28][CH2:27]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86598551(+/-)-3-[5-(Benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl]-2-hydroxypropyl 4-methylbenzenesulfonate

Product 1

HCID 86598552(+/-)-2-Hydroxy-3-(5-hydroxy-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl)propyl 4-methylbenzenesulfonateYield 92%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Treatment of (±)-3-[5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl]-2-hydroxypropyl 4-methylbenzenesulfonate (20.00 g, 38.3 mmol) with palladium on carbon (10 wt. %, 2.0 g) generally according to the procedure described for Intermediate 4 provided 15.18 g (92%) of (±)-2-hydroxy-3-(5-hydroxy-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-6-yl)propyl 4-methylbenzenesulfonate as a brown oil. Anal. calcd. for C23H28O6S: C, 63.34; H, 6.56. Found: C, 62.98; H, 6.66.

Sources & evidence

ORD record
ord-da225071373c42f58bb38328f63f50a3
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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