Sodium Thiosulfate → HCID 58313136, compound

HRID 1800780Notes

Reaction equation

HRID 1800780 reaction equation
[OH:1][CH:2]1[CH2:26][CH2:25][C:5]2([CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:6]2)[CH2:4][CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:1]=[C:2]1[CH2:3][CH2:4][C:5]2([CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[CH:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:6]2)[CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58313094HCID 58313094, compound

Product 1

HCID 58313136HCID 58313136, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-ethyl 2-(phenylmethyl) 8-hydroxy-2-azaspiro[4.5]decane-2,3-dicarboxylate (112) (4.36 g, 120.05 mmol) in dry DCM (60 mL) was added Dess-Martin Periodinane (10.22 g, 24.1 mmol) and the reaction stirred at rt under nitrogen for 18 h. The reaction was poured into 10% aq sodium thiosulfate (150 mL) and sat. NaHCO3 (150 mL) and stirred for 10 min. Extracted with DCM (2×150 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 25-80% hexanes/EtOAc to afford the title compound as a pale yellow oil (2.89 g, 67% yield).

Workup

  1. stirringstirred for 10 min
  2. extractionExtracted with DCM (2×150 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 25-80% hexanes/EtOAc

Sources & evidence

ORD record
ord-65dbc58f4e4f435cb3537546761333d8
Source dataset
uspto-grants-2013_01
Patent number
US08344155B2

Reaction notes

Loading…