Sodium Hydroxide → HCID 57109009, compound

HRID 1492005Notes

Reaction equation

HRID 1492005 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C@@H:12]1[C@@H:16]([O:17]C(=O)[C@@H](C2C=CC=CC=2)OC)[CH2:15][O:14][C@@H:13]1[C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C@H:12]1[C@@H:16]([OH:17])[CH2:15][O:14][C@@H:13]1[C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67811017HCID 67811017, compound

Product 1

HCID 57109009HCID 57109009, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.02 g (0.00416 mole) of (2S,3S,4R)-3-(3-t-butyldimethylsilyloxyprop-1-yl)-4-[(R)-(-)-α-methoxyphenylacetoxy)-2-(3-pyridyl)tetrahydrofuran, 8.32 ml (0.00832 mole) of 1N sodium hydroxide in 20 ml of methanol is stirred at room temperature for 1 h and evaporated. The residue is triturated with water and extracted with ethyl acetate (3×20 ml). The combined extracts are washed with water and brine, dried (MgSO4) and evaporated. The residue is purified by flash chromatography to give (2S,3S,4R)-3-(3-t-butyldimethylsilyloxyprop-1-yl)-4-hydroxy-2-(3-pyridyl)tetrahydrofuran as an oil with [α]D25 =+43.8 (MeOH).

Workup

  1. customevaporated
  2. customThe residue is triturated with water
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. washThe combined extracts are washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-f80ac117fcb2425c8d97db2de4795494
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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