Water → HCID 86728584, compound

HRID 1410297Notes

Reaction equation

HRID 1410297 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[C@@H:22]1[O:31][C@H:30]2[C@@H:25]([O:26][CH:27]([CH:32]=[CH2:33])[O:28][CH2:29]2)[C@H:24]([OH:34])[C@H:23]1[OH:35])[CH:2]=[CH2:3].C([BH3-])#N.[Na+].FC(F)(F)S(O)(=O)=O.O>O1CCCC1>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[C@H:22]1[C@H:23]([OH:35])[C@@H:24]([OH:34])[C@H:25]([OH:26])[C@@H:30]([CH2:29][O:28][CH2:27][CH:32]=[CH2:33])[O:31]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 62406Trifluoromethanesulfonic acidHCID 5003444Sodium cyanoborohydrideHCID 86728585HCID 86728585, compound

Product 1

HCID 86728584HCID 86728584, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (4aR,6S,7R,8R,8aS)-6-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-2-vinylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol (14, 669 mg, 1.33 mmol) from Step 1 in tetrahydrofuran (13 mL) was added sodium cyanoborohydride (642 mg, 9.71 mmol), molecular sieves (407 mg) and was added cautiously trifluoromethanesulfonic acid. After addition, the mixture was stirred for another 0.5 h, before being poured into H2O. The aqueous phase was extracted with dichloromethane and the combined organic fractions were washed with brine. The organic layer was dried over magnesium sulfate and filtered through a pad of silica gel. The filtrate was evaporated and went to next step.

Workup

  1. additionAfter addition
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. washthe combined organic fractions were washed with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered through a pad of silica gel
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-3e671c8bd5a140f69f7b8973fcbef860
Source dataset
uspto-grants-2014_12
Patent number
US08921412B2

Reaction notes

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