Sodium Thiosulfate → HCID 90200952, compound

HRID 718874Notes

Reaction equation

HRID 718874 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]12[CH2:28][CH2:27][C:22]3([O:26][CH2:25][CH2:24][O:23]3)[CH2:21][CH:9]1[CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[C:17]([CH:19]=[O:20])[N:16]=[CH:15][C:14]=12.[F:29][C:30]1[CH:35]=[CH:34][C:33]([Mg]Br)=[CH:32][CH:31]=1.[NH4+].[Cl-].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+]>C1COCC1>[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH:19]([C:17]2[N:16]=[CH:15][C:14]3[C@:8]4([CH2:7][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=5)[CH2:28][CH2:27][C:22]5([O:26][CH2:25][CH2:24][O:23]5)[CH2:21][C@H:9]4[CH2:10][CH2:11][CH2:12][C:13]=3[CH:18]=2)[OH:20])=[CH:32][CH:31]=1

Participants

8

Reactant 6

HCID 24477Sodium ThiosulfateHCID 25517Ammonium ChlorideHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86722481HCID 86722481, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 90200952HCID 90200952, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Rac-(7aR,11aS)-11a-(Pyridin-2-ylmethyl)-5,6,7,7a,8,10,11,11a-octahydro spiro[benzo[6,7]cyclohepta[1,2-c]pyridine-9,2′-[1,3]dioxolane]-3-carbaldehyde (146, R2=Pyridin-2-ylmethyl) (0.400 g, 1.06 mmol) and THF (10 mL) were added to a round bottom flask and stirred. (4-Fluorophenyl)magnesium bromide (2M in diethyl ether) (0.95 mL, 1.90 mmol) was added and the mixture was stirred at rt for about 1 h. Sat. aq. NH4Cl was added and the product was extracted with EtOAc (15 mL), dried over MgSO4 and concentrated in vacuo. The residue was taken into DCM (6 mL) and stirred at rt. Dess-Martin periodinane (0.556 g, 1.31 mmol) was added and mixture was stirred at rt for about 2 h. Sat. aq. NaHCO3 (5 mL) and sat. aq. Na2S2O3 (5 mL) were added and the resulting mixture was extracted with EtOAc (15 mL), dried over Na2SO4 and concentrated in vacuo.

Workup

  1. stirringthe mixture was stirred at rt for about 1 h
  2. extractionthe product was extracted with EtOAc (15 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. stirringstirred at rt
  6. stirringmixture was stirred at rt for about 2 h
  7. extractionthe resulting mixture was extracted with EtOAc (15 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3abfa689417e4b2cb489f2dcdcddd5fd
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

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