Sodium borohydride → HCID 178494573, compound

HRID 1900054Notes

Reaction equation

HRID 1900054 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]3)=[CH:12][N:11]=2)[CH2:5]1.[BH4-].[Na+]>CO.O>[OH:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([C:13]2[CH:14]=[CH:15][C:10]([N:6]3[CH2:5][CH:4]([CH2:3][O:2][CH3:1])[O:8][C:7]3=[O:9])=[N:11][CH:12]=2)[CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 23371888HCID 23371888, compound

Product 1

HCID 178494573HCID 178494573, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.4 g of (RS)-5-methoxymethyl-3-[5-(4-oxo-cyclohexyl)-pyridin-2-yl]-oxazolidin-2-one in 25 ml of methanol and 2.5 ml of water was treated with 0.2 g of sodium borohydride and stirred at room temperature for 16 h. Then, the mixture was concentrated and the residue was taken up in methylene chloride and washed with water. The aqueous phase was extracted with methylene chloride and the organic phases were combined, dried with magnesium sulfate and concentrated. The residue (0.4 g) was recrystallized from ethyl acetate and there was obtained 0.2 g of (RS)-3-[5-(trans-4-hydroxy-cyclohexyl)-pyridin-2-yl]-5-methoxymethyl-oxazolidin-2-one. M.p.: 142°-143°.

Workup

  1. concentrationThen, the mixture was concentrated
  2. washwashed with water
  3. extractionThe aqueous phase was extracted with methylene chloride
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue (0.4 g) was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a739d8da7d744abcb52fe4f8a5dd3ed1
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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