Hydrochloric Acid → HCID 58280177, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 2.0 g (8.647 mmol) of (1S,5R)-2-[(1R)-1-phenylethyl]-6-oxa-2-azabicyclo[3.2.1]octan-7-one [prepared from N-[(1R)-1-phenylethyl]but-3-en-1-amine according to Bioorg. Med. Chem. Lett. 6 (8), 964 (1996)] in 8 ml of abs. THF, cool to −78° C. and add 9.5 ml (9.5 mmol) of a 1M solution of L-Selectride in THF. After the end of the addition, continue stirring at −78° C. for 1 h, then warm to −20° C. and add 2.1 ml (13 mmol) of phosphonoacetic acid trimethyl ester. Then warm the reaction mixture to 0° C. and stir for 1 h. Water is then added and 1N hydrochloric acid is used to set a pH of approx. 7-8. Extract the mixture with dichloromethane three times, and combine the organic phases, dry over magnesium sulphate and concentrate under reduced pressure. 4.32 g of crude product are obtained, which are used without further purification in the next stage.

Provenance & Evidence