Sodium borohydride → HCID 497423, compound

HRID 1167457Notes

Reaction equation

HRID 1167457 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][O:20][C:21]4[CH:25]=[CH:24][O:23][N:22]=4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4][CH2:3]1.[BH4-].[Na+]>C(O)C>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][O:20][C:21]4[CH:25]=[CH:24][O:23][N:22]=4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69979965HCID 69979965, compound

Product 1

HCID 497423HCID 497423, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-(4-Oxopiperidin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (173 mg, 0.46 mmol) was dissolved in ethanol (5 ml), treated with sodium borohydride (18 mg, 0.48 mmol) and refluxed 1 hour. Solvent was evaporated, the residue treated with water (5 ml), neutralised with 1 N hydrochloric acid, extracted with dichloromethane (3×10 ml), and dried (magnesium sulfate). Evaporation gave the desired product (76 mg). MS (ESP): 378 (MH+) for C18H20FN3O5.

Workup

  1. temperaturerefluxed 1 hour
  2. customSolvent was evaporated
  3. additionthe residue treated with water (5 ml)
  4. extractionextracted with dichloromethane (3×10 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customEvaporation

Sources & evidence

ORD record
ord-fb1fbd4b30e24f669039c38140fcd3b3
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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