Tetrahydrofuran → HCID 53866615, compound

HRID 974880Notes

Reaction equation

HRID 974880 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:29][CH:30]=[CH2:31])[C@H:10]([N:26]=[N+:27]=[N-:28])[C:11](N2[C@@H](CC3C=CC=CC=3)COC2=O)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C1COCC1.[Li+].[BH4-]>CO>[N:26]([C@@H:10]([C@H:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:29][CH:30]=[CH2:31])[CH2:11][OH:12])=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 53941532HCID 53941532, compound

Product 1

HCID 53866615HCID 53866615, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(3(S)-(3,4-dichlorophenyl)-2(S)-azido-1-oxo-5-hexenyl)-4(S)-benzyl-2-oxazolidinone (890 mg, 1.94 mmol) and THF (25 mL) at 0° C. was added MeOH (126 mL, 3.1 mmoL), followed by LiBH4 (68 mg, 3.1 mmol). The mixture was allowed to stir for 2 h, and was then quenched by addition of sat. aq. Rochelle salts (50 mL) and was allowed to warm to room temp and stirred vigorously for 2 h. The mixture was diluted with H2O (150 mL) and extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel 60, 10-40% EtOAc/hexanes) to afford the alcohol (452 mg, 82%) as a colorless oil.

Workup

  1. customwas then quenched by addition of sat. aq. Rochelle salts (50 mL)
  2. stirringstirred vigorously for 2 h
  3. additionThe mixture was diluted with H2O (150 mL)
  4. extractionextracted with CH2Cl2 (3×100 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel 60, 10-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e7ecd51124164a8dada968df69d7554a
Source dataset
uspto-grants-1997_03
Patent number
US05607936

Reaction notes

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