Potassium Carbonate → {2-[7-Benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl]ethyl}tert-butyl-carbamate

HRID 1992336Notes

Reaction equation

Cl.Cl.[CH2:3]([N:10]1[CH2:17][CH:16]2[O:18][CH:12]([CH2:13][NH:14][CH2:15]2)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:19]([NH:23][C:24](=[O:29])[O:25][CH2:26][CH2:27]Br)([CH3:22])([CH3:21])[CH3:20].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:3]([N:10]1[CH2:17][CH:16]2[O:18][CH:12]([CH2:13][N:14]([CH2:27][CH2:26][O:25][C:24](=[O:29])[NH:23][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15]2)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane dihydrochloride (8 g, 0.0275 mol, 1.0 eq.; see WO 01/28992), 2-bromoethyl tert-butylcarbamate (9.23 g, 0.0412 g, 1.5 eq.) and fused K2CO3 (18.96 g, 0.1375 mol, 5.0 eq.) in dry acetonitrile (120 mL) was stirred at 70° C. overnight under a N2 atmosphere. The reaction mixture was cooled to RT, filtered and concentrated under reduced pressure. The resulting resiude was purified by column chromatography over silica gel (using 92:8 DCM:methanol as final eluent) to yield the sub-title compound (5 g, 43%).

Workup

temperatureThe reaction mixture was cooled to RT
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting resiude was purified by column chromatography over silica gel (using 92:8 DCM:methanol as final eluent)

Sources & evidence

ORD record: ord-872a0dc3244d4082970966248a8ba36c
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648985B2

Reaction notes

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