Benzyl Alcohol → HCID 14213078, compound

HRID 1722687Notes

Reaction equation

HRID 1722687 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[C:20]([O:24][C:25]([CH2:27][C@@H:28]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:29](N1[C@H](C(C)C)COC1=O)=[O:30])=[O:26])([CH3:23])([CH3:22])[CH3:21]>O1C=CC=C1.O1CCCC1>[CH2:1]([O:8][C:29](=[O:30])[C@H:28]([CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH2:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8058HexaneHCID 14213076(4R)-3-((2R)-3-t-butoxycarbonyl-2-benzylpropionyl)-4-(2-propyl)-oxazolidine-2-oneHCID 178418339Butyllithium

Product 1

HCID 14213078HCID 14213078, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8029FuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of dry benzyl alcohol (0.55 ml, 5.33 mmol) in anhydrous tetrahydron furan (18 ml) under a nitrogen atmosphere at 0° C. was added a hexane solution of n-butyllithium (2.58 ml; 4.00 mmol). To this solution was added the product from Example 141 in anhydrous tetrahydrofuran (10 ml). After stirring 1 h at 0° C. the reaction was quenched by adding excess saturated aqueous ammonium chloride. The volatiles were removed by rotary evaporation and the resulting aqueous residue extracted two times with ether. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo provided an oil which was purified by chromatography on SiO2 (15% ether acetate/hexanes) to provide the desired product (0.89 g, 94%) as a colorless oil. Mass spectrum: (M)+ =354.

Workup

  1. customwas quenched
  2. additionby adding excess saturated aqueous ammonium chloride
  3. customThe volatiles were removed by rotary evaporation
  4. extractionthe resulting aqueous residue extracted two times with ether
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customprovided an oil which
  10. customwas purified by chromatography on SiO2 (15% ether acetate/hexanes)

Sources & evidence

ORD record
ord-e3672f75231d45a889b58d213f13ebc7
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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