Ammonium Chloride → HCID 13567484, compound

HRID 595253Notes

Reaction equation

HRID 595253 reaction equation
[BH4-].[Na+].[CH3:3][C@H:4]1[O:8][C:7](=[O:9])[NH:6][C@@H:5]1[C:10](OC)=[O:11].[Cl-].[NH4+]>C(O)C>[OH:11][CH2:10][C@@H:5]1[C@@H:4]([CH3:3])[O:8][C:7](=[O:9])[NH:6]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 10725638HCID 10725638, compound

Product 1

HCID 13567484HCID 13567484, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.55 g, 14.65 mmol) was added to a mixture of (4S,5R)-methyl 5-methyl-2-oxooxazolidine-4-carboxylate (2.12 g, 13.32 mmol) in ethanol (29 mL) at 0° C. The mixture was stirred for 3 hours and then 2 mL of saturated aqueous ammonium chloride was added. The mixture was stirred for 30 minutes and the white solids were filtered through CELITE and the filter cake was washed with ethanol. The filtrate was concentrated under reduced pressure and dried under vacuum to afford (4R,5R)-4-(hydroxymethyl)-5-methyloxazolidin-2-one. 1H NMR (500 MHz, D2O) δ 4.56-4.37 (m, 1H), 3.60-3.38 (m, 3H), 1.27 (d, J=6.4 Hz, 3H).

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. filtrationthe white solids were filtered through CELITE
  3. washthe filter cake was washed with ethanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3bbdedd66f014b4c88c6364035f2ebe1
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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