Cesium carbonate → 8-Quinoxalin-2-yl-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester

HRID 1193055Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([NH:11][CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:17]1[CH:26]=[N:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([N:11]([C:17]3[CH:26]=[N:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)[CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester (Intermediate 1, 1.07 g, 5.05 mmol) and 2-chloro-quinoxaline (1.02 g, 6.06 mmol) in DMF (20.0 mL) was added Cs2CO3 (3.95 g, 12.1 mmol). The reaction mixture was heated at 80° C. for 16 h then cooled to ambient temperature. The reaction mixture was partitioned between water (400 mL) and ethyl acetate (50 mL) twice. The organic layers were combined and washed with water. The organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to yield crude title compound (1.84 g) which was used in the next step without purification.

Workup

temperaturethen cooled to ambient temperature
customThe reaction mixture was partitioned between water (400 mL) and ethyl acetate (50 mL) twice
washwashed with water
dry with materialThe organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f685c558b81243fe8cf4f58b4398bd1a
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680275B2

Reaction notes

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