Sodium borohydride → HCID 56617577, compound

HRID 280913Notes

Reaction equation

HRID 280913 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].[BH4-].[Na+]>O1CCCC1>[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

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13264147HCID 13264147, compound

Product 1

HCID 56617577HCID 56617577, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

16.48 g of (S)-3'-acetyl-1',2',3',4'-tetrahydro-3'-hydroxy-5',8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] were suspended in 1450 ml of dry tetrahydrofuran and 3.59 g of sodium borohydride were added to the mixture. The mixture was then stirred at room temperature under nitrogen for 4 hours. The solvent was removed by evaporation and the white residue was cooled to 0° C. 1500 ml of 5% ammonium chloride solution were added and the mixture was stirred at room temperature until the evolution of gas had ceased. The solution was extracted with three 500 ml portions of ethyl acetate and the combined ethyl acetate extracts were washed with 1000 ml of water, dried over magnesium sulphate and evaporated to give 17.65 g of (3'S)-1',2',3',4'-tetrahydro-3'-hydroxy-3'-(1-hydroxyethyl)-5',8'-dimethoxyspiro[1,3-dithiolane-2,1'-naphthalene] in the form of a colourless gum which was used without further purification.

Workup

  1. customThe solvent was removed by evaporation
  2. temperaturethe white residue was cooled to 0° C
  3. addition1500 ml of 5% ammonium chloride solution were added
  4. stirringthe mixture was stirred at room temperature until the evolution of gas
  5. extractionThe solution was extracted with three 500 ml portions of ethyl acetate
  6. washthe combined ethyl acetate extracts were washed with 1000 ml of water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-e3087b8f1b58438db8d79e22744a0295
Source dataset
uspto-grants-1986_05
Patent number
US04591636

Reaction notes

Loading…