Water → HCID 59593753, compound

HRID 1474595Notes

Reaction equation

HRID 1474595 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@:6]1([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([CH2:33][O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:27]=1)OC)(=[O:3])[CH3:2].C([SiH](CC)CC)C.O.B(F)(F)F.CCOCC>C(#N)C.C(OCC)(=O)C>[C:16]([O:15][C@H:9]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@H:6]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([CH2:33][O:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:27]=2)[O:7][C@@H:8]1[CH2:19][O:20][C:21](=[O:23])[CH3:22])(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 71117120HCID 71117120, compound

Product 1

HCID 59593753HCID 59593753, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,3R,4S,5R,6R)-6-(acetoxymethyl)-2-(4-chloro-3-(phenoxymethyl)phenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (12.00 g, 20.73 mmol), triethylsilane (10.46 mL, 65.51 mmol) and water (373 mg, 20.73 mmol) in ACN (62.18 mL) was added BF3.Et2O (5.21 mL, 41.46 mmol) at 0° C. The reaction was stirred at r.t. for 18 h. After the completion of reaction as confirmed by TLC, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated NaHCO3 (50 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 3:7 Ethyl acetate:Pet. Ether) to afford the title compound (10.58 g, 93%).

Workup

  1. customAfter the completion of reaction
  2. washwashed with saturated NaHCO3 (50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto afford crude product which
  6. customwas purified by column chromatography (silica gel, 3:7 Ethyl acetate:Pet. Ether)

Sources & evidence

ORD record
ord-bd3867b8b6134310bdc0fdbd3c28770a
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

Loading…