Benzyl Bromide → HCID 67075027, compound

HRID 1944078Notes

Reaction equation

HRID 1944078 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C:10](=[CH2:17])[O:9]2)=[CH:4][C:3]=1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=1.[H-].[Na+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[I-].[C:39]([NH3+])([CH3:42])([CH3:41])[CH3:40]>CN(C=O)C.O>[CH2:30]([O:14][C@@H:13]1[C@@H:12]([O:15][CH2:40][C:39]2[CH:42]=[CH:17][CH:10]=[CH:11][CH:41]=2)[C@H:11]([O:16][CH2:18][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)[C:10](=[CH2:17])[O:9][C@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH3:27])=[CH:23][CH:24]=2)[CH:4]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22344722t-Butylammonium IodideHCID 58592574HCID 58592574, compound

Product 1

HCID 67075027HCID 67075027, compoundYield 912.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,3R,4R,5S)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-methylene-tetrahydro-pyran-3,4,5-triol (300 mg, 0.77 mmole) in dry DMF (3 mL), sodium hydride (166 mg, 3.46 mmole) was added at 0° C. and stirred at room temperature for 2 hours. Benzyl bromide (0.3 mL, 2.54 mmole), t-butylammoniumiodide (10 mg) was added and reaction mixture stirred at room temperature for 18 hours. The reaction mixture was diluted with water (50 mL) and extracted with DCM (2×200 mL). The crude product was purified by silica gel column chromatography (2% ethylacetate in hexane) to furnish 300 mg of (2S,3S,4R,5S)-3,4,5-tris-benzyloxy-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-methylene-tetrahydro-pyran.

Workup

  1. customreaction mixture
  2. stirringstirred at room temperature for 18 hours
  3. extractionextracted with DCM (2×200 mL)
  4. customThe crude product was purified by silica gel column chromatography (2% ethylacetate in hexane)

Sources & evidence

ORD record
ord-e74b41d8b5a54682992b2dd415dee418
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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