Water → HCID 178472359, compound

HRID 928122Notes

Reaction equation

HRID 928122 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]([C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]2)[CH2:8][CH:9]=[CH2:10])=[N:4][CH:3]=1.C[N+]1([O-])CC[O:26]CC1.C1COCC1.[OH2:35]>S([O-])([O-])(=O)=S.[Na+].[Na+].[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[S:6][C:5]([CH:7]([C@H:11]2[CH2:12][CH2:13][C@H:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15][CH2:16]2)[CH2:8][CH:9]([OH:26])[CH2:10][OH:35])=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 178441596HCID 178441596, compound

Product 1

HCID 178472359HCID 178472359, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 24477Sodium ThiosulfateSolvent

Procedure

Ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)but-3-en-1-yl]cyclohexanecarboxylate (40 mg, 0.107 mmol), 4-methylmorpholine N-oxide (14 mg, 0.120 mmol), THF (0.8 ml), water (0.4 ml) and osmium tetroxide (0.2 ml, 0.025 mmol). The mixture was stirred at room temperature for 15 min. The mixture was diluted with 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 (0-100% EtOAc in hexane) to afford ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-3,4-dihydroxybutyl]cyclohexanecarboxylate. MS ESI calc'd. for C16H24BrNO4S [M+H]+ 406, 408. found 406, 408. 1H NMR (500 MHz, CDCl3) δ 7.54 (s, 1H), 4.08 (q, J=7.1, 2H), 3.70-2.93 (m, 3H), 2.60-2.42 (m, 1H), 2.25-2.06 (m, 1H), 2.06-1.51 (m, 7H), 1.51-1.30 (m, 2H), 1.22 (t, J=7.1, 3H), 1.14-0.92 (m, 2H).

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 (0-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-178d10c696b4477aa1a1836d51b8d3e7
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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