Hydrochloric Acid → (1S,2R)-(+)-Norephedrine
Reaction equation
Cl.[C:2]1([CH:8]([OH:19])[CH:9]([NH:11]C(OC(C)(C)C)=O)[CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[C:2]1([CH:8]([OH:19])[CH:9]([NH2:11])[CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
20 ml of 3N-hydrochloric acid solution and 10 ml of methanol were added into the above-described 1-phenyl-2-(t-butoxycarbonylamino)propanol in an amount of 1.05 g (4.00 mmol), and the resulting solution was stirred for an hour at an ambient temperature. Then, the methanol in the solution was distilled out, and the aqueous layer of the solution was separated by extraction with ethyl acetate. The aqueous layer was adjusted to alkaline state by adding aqueous solution of sodium hydroxide and was then extracted with chloroform. The obtained chloroform solution was dried with anhydrous magnesium sulfate and distilled under reduced pressure to obtain 1-phenyl-2-aminopropanol in an amount of 465 mg (2.48 mmol) at a yield of 77%.
Workup
- distillationThen, the methanol in the solution was distilled out
- customthe aqueous layer of the solution was separated by extraction with ethyl acetate
- additionby adding aqueous solution of sodium hydroxide
- extractionwas then extracted with chloroform
- dry with materialThe obtained chloroform solution was dried with anhydrous magnesium sulfate
- distillationdistilled under reduced pressure
Sources & evidence
- ORD record
- ord-bf59b5dc2a934e1f94c747864bb8ac70
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06410749B1
Reaction notes
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