Ethyl isocyanate → 8-(N-Ethylcarbamyl)-3-methyl-3,8-diazabicyclo[3.2.1]octane
Reaction equation
Cl.Cl.[CH3:3][N:4]1[CH2:10][CH:9]2[NH:11][CH:6]([CH2:7][CH2:8]2)[CH2:5]1.[CH2:12]([N:14]=[C:15]=[O:16])[CH3:13].C(N1C2CCC1CN(C)C2)(OCC)=O>>[CH2:12]([NH:14][C:15]([N:11]1[CH:9]2[CH2:8][CH2:7][CH:6]1[CH2:5][N:4]([CH3:3])[CH2:10]2)=[O:16])[CH3:13]Participants
4
Procedure
3-Methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (3.0 g, 0.0151 mole), prepared as described in Example 5, was reacted with 1.21 ml (0.0151 mole) ethyl isocyanate in a procedure as described for 8-carbethoxy-3-methyl-3,8-diazabicyclo[3.2.1]octane in Example 6. The crude desired product, as the free base, was purified by chromatography on alumina with chloroform elution. An hydrochloride salt was made by treatment of a solution of the free base in diethyl ether with ethanolic hydrogen chloride and filtering to collect 1.0 g (28% yield) white solid exhibiting a dual melting point of 100°-140° C and 191°-202° C until dried 2 hours at 126° C in vacuo after which the desired product hydrochloride salt melted at 205°-215° C.
Workup
- customThe crude desired product, as the free base, was purified by chromatography on alumina with chloroform elution
- filtrationfiltering
Sources & evidence
- ORD record
- ord-31524171196840dd87110835d3f1c93a
- Source dataset
- uspto-grants-1976_04
- Patent number
- US03951980
Reaction notes
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