Water → HCID 178472378, compound

HRID 928119Notes

Reaction equation

HRID 928119 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH2:8])=[N:4][CH:3]=1.C[N+]1([O-])CC[O:24]CC1.C1COCC1.[OH2:33]>S([O-])([O-])(=O)=S.[Na+].[Na+].[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)([OH:24])[CH2:8][OH:33])=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 178437588HCID 178437588, compound

Product 1

HCID 178472378HCID 178472378, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 24477Sodium ThiosulfateSolvent

Procedure

Ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)ethenyl]cyclohexanecarboxylate (40 mg, 0.12 mmol), 4-methylmorpholine N-oxide (31 mg, 0.27 mmol), THF (0.8 ml), water (0.4 ml) and osmium tetroxide (0.22 ml, 0.028 mmol) were combined and the mixture was stirred at room temperature for 40 min. The mixture was then diluted with saturated sodium thiosulfate and extracted with EtOAc. The organic phase was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified on silica gel (EtOAc/hexane=1/1) to afford racemic ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-1,2-dihydroxyethyl]cyclohexane-carboxylate. MS ESI calc'd. for C14H20BrNO4S [M+H]+ 378, 380. found 378, 380. 1H NMR (500 MHz, CDCl3) δ 7.55 (s, 1H), 4.15 (dd, J=5.7, 11.1, 1H), 4.07 (q, J=7.1, 2H), 3.74 (dd, J=7.0, 11.1, 1H), 2.61 (t, J=6.4, 1H), 2.20-2.10 (m, 1H), 2.05-1.84 (m, 3H), 1.85-1.70 (m, 1H), 1.60 (d, J=12.8, 1H), 1.46-1.13 (m, 5H), 1.13-1.05 (m, 1H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel (EtOAc/hexane=1/1)

Sources & evidence

ORD record
ord-a13af991b984464b872839fe04b2b7ff
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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