Sodium Thiosulfate → HCID 58230166, compound

HRID 2092713Notes

Reaction equation

HRID 2092713 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][C:13]3([CH2:20][CH2:19][CH:18]([CH:21]([OH:26])[C:22]([F:25])([F:24])[F:23])[CH2:17][CH2:16]3)[C:12]2=[O:27])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:30].C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.CCOC(C)=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:15][CH2:14][C:13]3([CH2:20][CH2:19][CH:18]([C:21]([OH:30])([OH:26])[C:22]([F:24])([F:25])[F:23])[CH2:17][CH2:16]3)[C:12]2=[O:27])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58229952HCID 58229952, compound

Product 1

HCID 58230166HCID 58230166, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-tert-butyl-phenyl)-8-(2,2,2-trifluoro-1-hydroxy-ethyl)-2-aza-spiro[4.5]decan-1-one (100 mg, 319 μmol, described in example 360 and 361) in DCM (1 mL) was added to a stirred suspension of Dess-Martin periodinane (501 mg, 1.18 mmol) in DCM (2.5 mL) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with EtOAc and poured into a 1:7 mixture of aqueous sat. NaHCO3 and Na2S2O3 and the mixture was stirred for 10 min. The organic phase was separated and washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give a crude residue which was purified by reverse phase prep HPLC to give the title compound as a white solid (94%). MS (m/e): 400.3 (MH+).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude residue which
  8. customwas purified by reverse phase prep HPLC

Sources & evidence

ORD record
ord-eb57c0ee03b34996aa6545f04d19e57e
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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