Sodium Thiosulfate → HCID 69027338, compound

HRID 1867221Notes

Reaction equation

HRID 1867221 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:15][CH:14]([CH3:16])[CH2:13][C:4]2([CH:10]([CH3:11])[CH2:9][C:8](=[O:12])[C:5]32[O:7][CH2:6]3)[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CC1(O)C2(CC(C)CC(C)(C)C2)C(C)CC1O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[OH:7][C:5]1([CH3:6])[C:4]2([CH2:13][CH:14]([CH3:16])[CH2:15][C:2]([CH3:17])([CH3:1])[CH2:3]2)[CH:10]([CH3:11])[CH2:9][C:8]1=[O:12]

Participants

9

Reactant 6

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 11447722HCID 11447722, compoundHCID 11470500HCID 11470500, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 69027338HCID 69027338, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Following the procedure detailed in Example 1,1,4,7,7,9-pentamethylspiro-[4.5]decan-1,2-diol was prepared by reduction of 6,6,8,10-tetramethyl-1-oxadispiro-[2.0.5.3]dodecan-12-one with lithium aluminum hydride. A solution of Dess-Martin periodinane (780 mg, 1.84 mmol) in CH2Cl2 (20 mL) was added in one dash to a stirred solution of 1,4,7,7,9-pentamethylspiro[4.5]decan-1,2-diol (400 mg, 1.66 mmol) in CH2Cl2 (15 mL). Stirring was continued at room temperature for 6 h, prior to quenching by dropwise addition of a solution of Na2S2O3 (950 mg, 6.00 mmol) in satd. aq. NaHCO3 (40 mL). After stirring for 30 min., water (50 mL) was added, the organic layer was separated, and the aqueous one extracted with CH2Cl2 (50 mL). The combined organic extracts were washed with water (50 mL), dried (Na2SO4), vacuum-filtrated over a pad of Celite®, and concentrated on the rotary evaporator. The resulting residue (430 mg) was separated by repeated silica-gel FC (pentane/Et2O, 9:1, Rf=0.48) to finally provide the weaker, less polar (1R*,4R*,5S*,9R*)-configured diastereoisomer of 1-hydroxy-1,4,7,7,9-pentamethylspiro[4.5]decan-2-one (60 mg, 15%) in pure form as colorless crystals, mp. 72-73° C.

Workup

  1. stirringAfter stirring for 30 min.
  2. customthe organic layer was separated
  3. extractionthe aqueous one extracted with CH2Cl2 (50 mL)
  4. washThe combined organic extracts were washed with water (50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationvacuum-filtrated over a pad of Celite®
  7. concentrationconcentrated on the rotary evaporator
  8. customThe resulting residue (430 mg) was separated

Sources & evidence

ORD record
ord-60fc84ba34274ddb9acd2b1f56091ef2
Source dataset
uspto-grants-2009_12
Patent number
US07632791B2

Reaction notes

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