HCID 88541262, compound → HCID 71152244, compound

HRID 1481608Notes

Reaction equation

HRID 1481608 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH:18]=[O:19])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:20]([CH3:22])[CH3:21])[S:14]2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][Mg+].[Br-]>C1COCC1.O>[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH:18]([OH:19])[CH3:23])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:20]([CH3:22])[CH3:21])[S:14]2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 88541262HCID 88541262, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 71152244HCID 71152244, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3aR,5S,6S,7aR)-6-(benzyloxy)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-5-carbaldehyde (1.04 g) in anhydrous THF (30 mL) at 0° C. was added a solution of MeMgBr (1.4 M in 1:3 THF/toluene, 5.80 mL, 8.13 mmol) dropwise. The reaction was then stirred at room temperature for 20 h. The mixture was diluted with H2O (50 mL), extracted with EtOAc (2×40 mL). The combined extract was dried over anhydrous Na2SO4. The solvents were evaporated under reduced pressure, and the residue was purified by silica gel column chromatography, eluted with 2%-5% 2 M NH3 MeOH solution in DCM to give 1-((3aR,5R,6S,7aR)-6-(benzyloxy)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)ethanol (0.840 g, 77%) as a pale yellow foam. MS m/z 337.2 (M+1, 100%); 1H NMR (400 MHz, CDCl3) shown this was a mixture of two diastereomers with a ratio ˜60:40.

Workup

  1. extractionextracted with EtOAc (2×40 mL)
  2. extractionThe combined extract
  3. dry with materialwas dried over anhydrous Na2SO4
  4. customThe solvents were evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography
  6. washeluted with 2%-5% 2 M NH3 MeOH solution in DCM

Sources & evidence

ORD record
ord-9ccffc3f4f924041b82037daaf24550f
Source dataset
uspto-grants-2016_08
Patent number
US09409924B2

Reaction notes

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