4-Chloroquinoline → tert-Butyl (1S,4S)-5-(4-quinolyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

HRID 333941Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C@H:12]12[CH2:18][C@H:15]([NH:16][CH2:17]1)[CH2:14][N:13]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>COCC(O)C>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([N:16]2[CH2:17][C@@H:12]3[CH2:18][C@H:15]2[CH2:14][N:13]3[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 115 °C

Procedure

4-Chloroquinoline (163.6 mg, 1 mmol) dissolved in 1-methoxy-2-propanol (4 ml) was added to tert-butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (237 mg, 1.2 mmol) and stirred at 115° C. for 72 hours. The solvent was removed under reduced pressure and the residue obtained (325 mg) was used directly in the next step. MS (APCI) m/z=326.0 [M+H]+.

Workup

customThe solvent was removed under reduced pressure
customthe residue obtained (325 mg)

Sources & evidence

ORD record: ord-9daeb34c9c474fa8b2fa00f8672bf862
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883791B2

Reaction notes

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