(S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester → (S)-3-(5-Pyrrolidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile

HRID 1791372Notes

Reaction equation

HRID 1791372 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[N:14]=1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=2)[C:24]#[N:25])[N:14]=1

Participants

4

Reactant 1

HCID 69619344(S)-2-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69619317(S)-3-(5-Pyrrolidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrileYield 73.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(S)-3-(5-Pyrrolidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile (360 mg, 73%) was prepared according to the procedure in Example 39 from (S)-2-[3-(3-cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (697 mg, 2.05 mmol) in dichloromethane (15 mL) and trifluoroacetic acid (2.4 mL) at room temperature for 2 h. 1H NMR (CDCl3), δ(ppm): 8.39 (s, 1H), 8.32 (d, 1H), 7.78 (d, 1H), 7.60 (t, 1H), 4.58 (dd, 1H), 3.22 (m, 1H), 3.13 (m, 1H), 2.34 (m, 1H), 2.14 (m, 1H), 2.00 (m, 3H).

Sources & evidence

ORD record
ord-360a41b080bd4cfe8db20293b3a3bb42
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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