Sodium Thiosulfate → (S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate

HRID 1907269Notes

Reaction equation

HRID 1907269 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH2:20][CH:21]([OH:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.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+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH2:20][C:21](=[O:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59190371tert-butyl (S)-1-(4-bromophenyl)ethyl(4-hydroxy-4-phenylbutyl)carbamate

Product 1

HCID 59190380(S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamateYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl (S)-1-(4-bromophenyl)ethyl(4-hydroxy-4-phenylbutyl)carbamate (3.24 g, 7.1 mmol) in CH2Cl2 (20 mL) at rt was added 15% Dess-Martin periodinane solution in CH2Cl2 (23 mL, 10.8 mmol). The mixture was stirred overnight at rt. Satd aq NaHCO3 (50 mL) was added and the mixture was stirred for 10 min. Solid Na2S2O3 (5 g) was added and stirring was continued for 1 h. The mixture was extracted with CH2Cl2 (2×100 mL) and the combined organic layer was washed with brine (35 mL) and dried over Na2SO4. Removal of the solvent left an amber oil (3.19 g) which was purified by chromatography on a 40-g silica cartridge eluted with a 0-100% EtOAc in hexanes gradient to afford (S)-tert-butyl 1-(4-bromophenyl)ethyl(4-oxo-4-phenylbutyl)carbamate (2.32 g, 72%) as a yellow oil. LC-MS Method 1 tR=2.40 min, m/z=470, 468, 348, 346.

Workup

  1. stirringthe mixture was stirred for 10 min
  2. stirringstirring
  3. waitwas continued for 1 h
  4. extractionThe mixture was extracted with CH2Cl2 (2×100 mL)
  5. washthe combined organic layer was washed with brine (35 mL)
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent
  8. waitleft an amber oil (3.19 g) which
  9. customwas purified by chromatography on a 40-g silica cartridge
  10. washeluted with a 0-100% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-ce2d91b46f8d4f808d5ced612efb76d4
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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