HCID 57049780, compound → HCID 57297511, compound

HRID 1492007Notes

Reaction equation

HRID 1492007 reaction equation
[C:1]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C@H:9]2[CH2:13][O:12][C@H:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C@@H:10]2[CH2:20][CH2:21][CH2:22][O:23][Si](C(C)(C)C)(C)C)=[CH:3][CH:2]=1>CO.Cl>[C:1]1([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:2]=[CH:3][C:4]([CH2:7][O:8][C@H:9]2[CH2:13][O:12][C@H:11]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C@@H:10]2[CH2:20][CH2:21][CH2:22][OH:23])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 57049780HCID 57049780, compound

Product 1

HCID 57297511HCID 57297511, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 1.37 g (0.00272 mole) of (2S,3S,4R)-4-(biphenyl-4-ylmethoxy)-3-(3-t-butyldimethylsilyloxyprop-1-yl)-2-(3-pyridyl)tetrahydrofuran in 14 ml of methanol, hydrogen chloride gas is bubbled until the pH of the solution is brought to 3. The mixture is stirred at room temperature for 1 h and evaporated. The residue is triturated with ethyl acetate and neutralized with concentrated aqueous sodium bicarbonate. The aqueous layer is extracted once more with ethyl acetate and the combined organic extracts are dried (MgSO4) and evaporated. The residue is purified by flash chromatography using methylene chloride-methanol-ammonium hydroxide (300:25:1) as eluent to give (2S,3S,4R)-4-(biphenyl-4-ylmethoxy)-3-(3-hydroxyprop-1-yl)-2-(3-pyridyl)tetrahydrofuran as an oil having [α]D25 =+89.78° (MeOH).

Workup

  1. customevaporated
  2. customThe residue is triturated with ethyl acetate and neutralized with concentrated aqueous sodium bicarbonate
  3. extractionThe aqueous layer is extracted once more with ethyl acetate
  4. dry with materialthe combined organic extracts are dried (MgSO4)
  5. customevaporated
  6. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-99c992816e7b4cc993f03e324e5969a4
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

Loading…