Water → HCID 46890322, compound

HRID 1013608Notes

Reaction equation

HRID 1013608 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C@H:15]([CH2:19][N:20]2[CH2:23][CH:22]([OH:24])[CH2:21]2)[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:6][CH:7]=1.[OH:25]OS([O-])=O.[K+].[OH2:31]>CO.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C@H:15]([CH2:19][N:20]2[CH2:21][CH:22]([OH:24])[CH2:23]2)[CH2:14][CH2:13][CH2:12]3)(=[O:25])=[O:31])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 59207197HCID 59207197, compound

Product 1

HCID 46890322HCID 46890322, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-[(R)-6-(3-fluoro-phenylsulfanyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-azetidin-3-ol (0.08 g, 0.23 mmol) in MeOH (4 mL) was added a solution of OXONE™ (0.307 g, 0.5 mmol) in 2.5 mL water. The reaction mixture was stirred at room temperature for 36 hours. The mixture was taken up in EtOAc, and the organic layer was washed with 1.5 M aqueous sodium carbonate, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by preparative TLC (hexanes/EtOAc/MeOH 5:4:1 to give 0.06 g of 1-[(R)-6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-azetidin-3-ol, MS M+H=376.

Workup

  1. washthe organic layer was washed with 1.5 M aqueous sodium carbonate
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative TLC (hexanes/EtOAc/MeOH 5:4:1

Sources & evidence

ORD record
ord-55478bb242ca417b8a5a66dd7fa840d3
Source dataset
uspto-grants-2011_07
Patent number
US07981923B2

Reaction notes

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