Hydrochloric Acid → HCID 58280177, compound
Reaction equation
[C:1]1([C@H:7]([N:9]2[CH2:15][CH2:14][C@@H:13]3[CH2:16][C@H:10]2[C:11](=O)[O:12]3)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[CH3:32][O:33][C:34]([CH2:36]P(OC)(OC)=O)=[O:35].Cl>C1COCC1.O>[CH3:32][O:33][C:34](=[O:35])/[CH:36]=[CH:11]/[C@@H:10]1[CH2:16][C@H:13]([OH:12])[CH2:14][CH2:15][N:9]1[C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8]Participants
Conditions
- Temperature
- -78 °C
Procedure
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.
Workup
- additionAfter the end of the addition
- temperaturewarm to −20° C.
- temperatureThen warm the reaction mixture to 0° C.
- stirringstir for 1 h
- extractionExtract the mixture with dichloromethane three times
- dry with materialdry over magnesium sulphate
- concentrationconcentrate under reduced pressure
Sources & evidence
- ORD record
- ord-77303eaf5bd64341a545b0585c439d7d
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324222B2
Reaction notes
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