Sodium Sulfite → HCID 58456266, compound

HRID 410472Notes

Reaction equation

HRID 410472 reaction equation
[OH:1][C:2]1([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.C1C(=O)N([Br:25])C(=O)C1.[O-]S([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[Br:25][C:15]1[S:14][C:13]([C:2]2([OH:1])[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]2)=[N:17][CH:16]=1

Participants

6

Reactant 3

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 90240746HCID 90240746, compound

Product 1

HCID 58456266HCID 58456266, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product of Step 1 (23.5 g, 92 mmol) was dissolved in DMF (94 mL) and then treated with NBS (19.66 g, 110 mmol) and stirred at RT for 10 hours. The reaction was then treated with Na2SO3 (5.8 g, 465 mmol) in H2O (150 mL) and then extracted with EtOAc (100 mL) and the oil was purified by flash chromatography on silica gel to afford ethyl 4-(5-bromo-1,3-thiazol-2-yl)-4-hydroxycyclohexanecarboxylate as an oil (31 g, 77 mmol), which was subjected to chiral chromatography to afford ethyl cis-4-(5-bromo-1,3-thiazol-2-yl)-4-hydroxycyclohexane-carboxylate as an oil (15 g, 33 mmol). MS ESI: [M+H]+ m/z 333.

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. customthe oil was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-84ff588677d1478283210ff5a944919f
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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