Hydrochloric Acid → HCID 56617577, compound

HRID 370591Notes

Reaction equation

[C:1]([C@:4]1([OH:22])[CH2:13][C:12]2[C:7](=[C:8]([O:16][CH3:17])[CH:9]=[CH:10][C:11]=2[O:14][CH3:15])[C:6]2([S:21][CH2:20][CH2:19][S:18]2)[CH2:5]1)(=[O:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.O>O1CCCC1.C(OCC)C>[OH:22][C@@:4]1([CH:1]([OH:3])[CH3:2])[CH2:13][C:12]2[C:7](=[C:8]([O:16][CH3:17])[CH:9]=[CH:10][C:11]=2[O:14][CH3:15])[C:6]2([S:18][CH2:19][CH2:20][S:21]2)[CH2:5]1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 10.0 g of (S)-3'-acetyl-1',2',3',4'-tetrahydro-3'-hydroxy-5',8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] in 250 ml of dry tetrahydrofuran was cooled to -78° C. and a solution of 1.12 g of lithium aluminium hydride in 75 ml of diethyl ether was added over a period of a few minutes. The mixture was stirred at -78° C. under nitrogen for 30 minutes and then a further 1.12 g of lithium aluminium hydride in 75 ml of diethyl ether were added. After a total reaction time of 45 minutes, 250 ml of 2M hydrochloric acid were added cautiously to the mixture and then 750 ml of water were added. The mixture was extracted with three 600 ml portions of dichloromethane and the combined extracts were washed with 300 ml of water, dried over magnesium sulphate and evaporated to give (3'S)-1',2',3',4'-tetrahydro-3'-hydroxy-3'-[1-(hydroxy)ethyl]-5', 8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] is a mixture of isomers in the form of a colourless gum which was used without further purification.

Workup

extractionThe mixture was extracted with three 600 ml portions of dichloromethane
washthe combined extracts were washed with 300 ml of water
dry with materialdried over magnesium sulphate
customevaporated

Sources & evidence

ORD record: ord-7c6b2bcf01cd44c7a03d19a89d20eeda
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04526960

Reaction notes

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