Acetyl trifluoroacetate → 2-Azatricyclo[3.3.1.13,7]decane-5-carboxamide
Reaction equation
[C:1]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([N:7]3C(OC(C)(C)C)=O)[CH2:5]1)[CH2:11]2)(=[O:3])[NH2:2].C(OC(=O)C(F)(F)F)(=O)C>C(Cl)Cl>[CH:6]12[CH2:5][C:4]3([C:1]([NH2:2])=[O:3])[CH2:11][CH:10]([CH2:9][CH:8]([CH2:13]3)[NH:7]1)[CH2:12]2Participants
4
Conditions
- Temperature
- 0 °C
Procedure
To a 100 mL RB flask fitted with magnetic stirrer was charged tert-butyl 5-carbamoyl-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate, Intermediate-11 (0.1 g, 0.0357 mmol) in DCM (5 mL). The reaction mixture was cooled to 0° C. and trifluoroacetic acetic anhydride (0.21 g, 0.17 mmol) was added and stirred for 4 hours. After completion of the reaction (reaction was monitored by LCMS) reaction mixture was concentrated followed by trituration with mixture of hexane:ether (1:1) to give Intermediate-12 (0.09 g, yield=90%).
Workup
- customTo a 100 mL RB flask fitted with magnetic stirrer
- customAfter completion of the reaction (reaction was monitored by LCMS) reaction mixture
- concentrationwas concentrated
- additionfollowed by trituration with mixture of hexane:ether (1:1)
- customto give Intermediate-12 (0.09 g, yield=90%)
Sources & evidence
- ORD record
- ord-8335c254284d4d54b47d7308448371f4
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303016B2
Reaction notes
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