Ammonia → HCID 58604491, compound

450 ml of ammonia were condensed at −78° C. 4.4 g of sodium were added in 4 portions at an interval of 10 min each time, and the mixture was stirred for 20 min. At −60° C., a solution of 9.8 g of tert-butyl (3S,5S,6R)-3-allyl-3-benzyloxymethyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate and 11.2 ml of ethanol in 150 ml of THF was added dropwise thereto. The mixture was stirred at −45° C. for 1.5 h, and the reaction was stopped by adding solid ammonium chloride until the blue color disappeared. The ammonia was then allowed to evaporate off, and 400 ml of water were added to the residue. The THF was removed in vacuo. The aqueous was adjusted to pH 2 with 1 N HCl and extracted 3 times with 200 ml of ethyl acetate each time. The combined organic phases were dried with MgSO4. The solvents were removed in vacuo and the residue was purified by chromatography on silica gel.

1. customcondensed at −78° C
2. stirringThe mixture was stirred at −45° C. for 1.5 h
3. customto evaporate off
4. addition400 ml of water were added to the residue
5. customThe THF was removed in vacuo
6. extractionextracted 3 times with 200 ml of ethyl acetate each time
7. dry with materialThe combined organic phases were dried with MgSO4
8. customThe solvents were removed in vacuo
9. customthe residue was purified by chromatography on silica gel

ORD record

ord-6988c573eecd49dfb2c8bef1323b341c

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07008957B2