Ethanol → HCID 59226561, compound

HRID 2046814Notes

Reaction equation

HRID 2046814 reaction equation
C([C@@H]1COC(=O)N1[C:14](=[O:33])[C@H:15]([CH3:32])[C@@H:16]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[C@H:17]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18]1)C1C=CC=CC=1.C(O)C.[Li+].[BH4-]>C1COCC1.C(OCC)C.[OH-].[Na+]>[Si:25]([O:24][C@@H:16]([C@H:17]1[CH2:21][O:20][C:19]([CH3:22])([CH3:23])[O:18]1)[C@@H:15]([CH3:32])[CH2:14][OH:33])([C:28]([CH3:31])([CH3:29])[CH3:30])([CH3:26])[CH3:27]

Participants

7

Reactant 3

HCID 702EthanolHCID 4148881Lithium borohydride2×HCID 67134258HCID 67134258, compound

Product 1

HCID 59226561HCID 59226561, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (R)-4-benzyl-3-((2R,3R)-3-(tert-butyldimethylsilyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropanoyl)oxazolidin-2-one (1.0 equiv.) and ethanol (3.0 equiv.) in THF (0.09 M) was added LiBH4 (1.0 equiv.) at −40° C. The reaction mixture was allowed to warm up to rt slowly and stirred at that temperature for 12 hours. The solution was cooled back to −40° C. and additional LiBH4 (0.3 equiv.) was added. After warming back up to rt and stirring for 2 hours the solution was then diluted with diethyl ether and 1N NaOH) was added. The resulting mixture was extracted with ethyl acetate, the organic layer was separated, washed with NaCl(sat.), dried over magnesium sulfate, filtered, and concentrated. The residue was purified via silica gel column chromatography (10-30% EtOAc/n-heptanes) yielding (2S,3R)-3-(tert-butyldimethylsilyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropan-1-ol in (75%). LC/MS=247.1 (M+H-ketal-H2O), Rt=0.64 min.

Workup

  1. temperatureThe solution was cooled back to −40° C.
  2. temperatureAfter warming back up to rt
  3. stirringstirring for 2 hours the solution
  4. additionwas added
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. customthe organic layer was separated
  7. washwashed with NaCl(sat.)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified via silica gel column chromatography (10-30% EtOAc/n-heptanes)

Sources & evidence

ORD record
ord-43999d2693b949f0b7563b957dbbb96c
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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