Sodium borohydride → HCID 13264151, compound

HRID 462632Notes

Reaction equation

HRID 462632 reaction equation
[OH:1][C:2]1([C:20](OC)=[O:21])[CH2:11][C:10]2([S:15][CH2:14][CH2:13][S:12]2)[C:9]2[C:4](=[C:5]([O:18][CH3:19])[CH:6]=[CH:7][C:8]=2[O:16][CH3:17])[CH2:3]1.[BH4-].[Na+]>O1CCCC1>[OH:1][C:2]1([CH2:20][OH:21])[CH2:3][C:4]2[C:9](=[C:8]([O:16][CH3:17])[CH:7]=[CH:6][C:5]=2[O:18][CH3:19])[C:10]2([S:12][CH2:13][CH2:14][S:15]2)[CH2:11]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13264142HCID 13264142, compound

Product 1

HCID 13264151HCID 13264151, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g of methyl rac-1',2',3',4'-tetrahydro-2'-hydroxy-5',8'-dimethoxyspiro[1,3-dithiolane-2,4'-naphthalene]-2'-carboxylate, prepared as described in Example 4(iv), were dissolved in 200 ml of dry tetrahydrofuran and 2.0 g of sodium borohydride were added to the solution. The resulting mixture was stirred at room temperature under nitrogen for 20 hours. The solvent was removed by evaporation and 100 ml of 10% ammonium chloride solution were added. The mixture was extracted with three 30 ml portions of ethyl acetate. The extracts were dried and evaporated to give a colourless oil. Crystallization of this oil from ethyl acetate/petroleum ether gave 1.6 g (87%) of rac-1',2',3',4'-tetrahydro-3'-hydroxy-3'-hydroxymethyl-5',8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] of melting point 132.5°-133.5° C.

Workup

  1. customThe solvent was removed by evaporation and 100 ml of 10% ammonium chloride solution
  2. additionwere added
  3. extractionThe mixture was extracted with three 30 ml portions of ethyl acetate
  4. customThe extracts were dried
  5. customevaporated
  6. customto give a colourless oil
  7. customCrystallization of this oil from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-63edb4f893a84deebed480f6608ccc60
Source dataset
uspto-grants-1985_05
Patent number
US04515969

Reaction notes

Loading…