Hydrochloric Acid → (R(R*,R*))-2-Amino-1-(p-(methylsulphonyl)phenyl)propane-1,3-diol

HRID 1879338Notes

Reaction equation

HRID 1879338 reaction equation
C([O:3][C:4](=O)[C@@H:5]([NH2:18])[C@@H:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[OH:7])C.[BH4-].[K+].Cl.O>CO>[NH2:18][C@H:5]([CH2:4][OH:3])[C@@H:6]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][CH:13]=1)[OH:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4192641Potassium borohydrideHCID 34175685(2S,3R)-Ethyl-2-amino-3-[4-(methylsulfonyl)phenyl]-3-hydroxy-propanoate

Product 1

HCID 6452441(R(R*,R*))-2-Amino-1-(p-(methylsulphonyl)phenyl)propane-1,3-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S,3R)-Ethyl-2-amino-3-[4-(methylsulfonyl)phenyl]-3-hydroxy-propanoate (Compound VIc) (10 g, 0.0348 moles) in methanol (about 100 mL) is reacted in a reaction vessel with potassium borohydride (about 2.8 g, 0.0522 moles) over about 6 hours while maintaining the temperature below about 60° C. The reaction is cooled to ambient room temperature and about 1N HCl and water (about 75 mL) are added. Thereafter, the solution is heated to evaporate the methanol. Next, sodium hydroxide is added (about 25%), the resulting solids are filtered and washed with water, then dried to yield (1R,2R)-2-amino-1-[4-(methylsulfonyl)phenyl]-1,3-propanediol (Compound V wherein R1 is methylsulfonyl).

Workup

  1. temperaturewhile maintaining the temperature below about 60° C
  2. temperatureThereafter, the solution is heated
  3. customto evaporate the methanol
  4. additionNext, sodium hydroxide is added (about 25%)
  5. filtrationthe resulting solids are filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-311253c4149e445aa90e865a3291f6be
Source dataset
uspto-grants-2012_11
Patent number
US08314252B2

Reaction notes

Loading…