Sodium Thiosulfate → HCID 86623653, compound

HRID 1158533Notes

Reaction equation

HRID 1158533 reaction equation
[CH2:1]([C@@:8]([OH:28])([CH2:25][CH2:26][OH:27])[C:9]([N:11]1[C@H:15]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[CH2:22][C@H:14]2[O:13][C:12]1([CH3:24])[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.CCOCC>[CH2:1]([C@:8]([OH:28])([C:9]([N:11]1[C@H:15]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[CH2:22][C@H:14]2[O:13][C:12]1([CH3:23])[CH3:24])=[O:10])[CH2:25][CH:26]=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 44819176HCID 44819176, compound

Product 1

HCID 86623653HCID 86623653, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (R)-2-benzyl-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3 aH-indeno[1,2-d]oxazol-3-yl)-2,4-dihydroxybutan-1-one (47) (0.12 g, 0.31 mmol) in dry CH2Cl2 (5 mL) was added over 1 min to a stirred solution of Dess-Martin periodinate (0.146 g, 0.35 mmol) in dry CH2Cl2 (10 mL). After 30 min the homogeneous mixture was diluted with ether and poured into cold saturated NaHCO3 (10 mL) containing Na2S2O3 (2.2 g). The organic layer was washed with aqueous saturated NaHCO3, brine and dried (MgSO4). The solvents were evaporated below 20° C. to give the title compound (0.086 g, 72%). The residue was immediately used for the next step.

Workup

  1. washThe organic layer was washed with aqueous saturated NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. customThe solvents were evaporated below 20° C.

Sources & evidence

ORD record
ord-d6bf8140c546447db3c076afdbc8bd56
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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