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

HRID 219607Notes

Reaction equation

HRID 219607 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. additionwas added
  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-4a7982521c8149f783b9a0eab907eafa
Source dataset
uspto-grants-2012_06
Patent number
US08202857B2

Reaction notes

Loading…