Sodium Thiosulfate → HCID 86660735, compound

HRID 932192Notes

Reaction equation

HRID 932192 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]([N:23]1[C@H:28]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[C@@H:27]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)[CH2:26][C@@:25]([CH2:44][OH:45])([CH3:43])[C:24]1=[O:46])[CH2:21][CH3:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Si:1]([O:18][CH2:19][C@@H:20]([N:23]1[C@H:28]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)[C@@H:27]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)[CH2:26][C@:25]([CH3:43])([CH:44]=[O:45])[C:24]1=[O:46])[CH2:21][CH3:22])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 67999214HCID 67999214, compound

Product 1

HCID 86660735HCID 86660735, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (3R,5R,6S)-1-((S)-1-(tert-butyldiphenylsilyloxy)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-(hydroxymethyl)-3-methylpiperidin-2-one (210 mg, 0.311 mmol; Example 248, Step B) in CH2Cl2 (8 mL) at 0° C. was added NaHCO3 (131 mg, 1.56 mmol) and Dess Martin periodinane (158 mg, 0.373 mmol) in one portion. The reaction was stirred at rt for 2 hours. The reaction was diluted with CH2Cl2 (30 mL) and treated with Na2S2O3 (15 mL, saturated aqueous solution) and NaHCO3 (15 mL, saturated aqueous solution) at rt for 2 hours. The separated aqueous layer was extracted with CH2Cl2 (2×50 mL) and the combined organic extracts were dried over MgSO4, filtered and evaporated in vacuo to give the title compound.

Workup

  1. extractionThe separated aqueous layer was extracted with CH2Cl2 (2×50 mL)
  2. dry with materialthe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5ea214ff1aff444ea1b0b8f4240a0c41
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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