Trifluoroacetic acid → 2-Azatricyclo[3.3.1.13,7]decane-5-carbonitrile
Reaction equation
[C:1]([C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([N:6]3C(OC(C)(C)C)=O)[CH2:4]1)[CH2:10]2)#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH:7]12[CH2:12][C:3]3([C:1]#[N:2])[CH2:10][CH:9]([CH2:11][CH:5]([CH2:4]3)[NH:6]1)[CH2:8]2Participants
4
Conditions
- Temperature
- 0 °C
Procedure
A 50 mL RB flask fitted with magnetic stirrer was charged with tert-butyl 5-cyano-2-azatricyclo[3.3.1.13,7]decane-2-carboxylate, Intermediate-13 (0.5 g, 1.98 mmol) in DCM (5 mL). Then reaction mixture was cooled to 0° C. and trifluoroacetic acid (1.1 g, 9.54 mmol) was added and stirred for 4 hours. After completion of the reaction (reaction was monitored by LCMS) the reaction mixture was concentrated followed by the process of trituration with mixture of hexane:ether (1:1) to give Intermediate-14 (0.5 g, yield=97%).
Workup
- customA 50 mL RB flask fitted with magnetic stirrer
- customThen reaction mixture
- customAfter completion of the reaction (reaction was monitored by LCMS) the reaction mixture
- concentrationwas concentrated
- additionfollowed by the process of trituration with mixture of hexane:ether (1:1)
- customto give Intermediate-14 (0.5 g, yield=97%)
Sources & evidence
- ORD record
- ord-686783ade78747358f75985f8a3760f0
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303016B2
Reaction notes
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