Ethyl chloroformate → 3-Carbethoxy-8-methyl-3,8-diazabicyclo[3.2.1]octane

HRID 1605939Notes

Reaction equation

Cl.Cl.[CH3:3][N:4]1[CH:9]2[CH2:10][CH2:11][CH:5]1[CH2:6][NH:7][CH2:8]2.Cl[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(CC)C(N1CC2N(C)C(CC2)C1)=O)C>>[C:13]([N:7]1[CH2:6][CH:5]2[N:4]([CH3:3])[CH:9]([CH2:10][CH2:11]2)[CH2:8]1)([O:15][CH2:16][CH3:17])=[O:14]

Participants

Reactant 3

HCID 10928Ethyl chloroformate

HCID 423352N,N-diethyl-8-methyl-3,8-diazabicyclo[3.2.1]octane-3-carboxamide

HCID 221201898-Methyl-3,8-diazabicyclo(3.2.1)octane dihydrochloride

Product 1

HCID 4233503-Carbethoxy-8-methyl-3,8-diazabicyclo[3.2.1]octaneYield 73%

Procedure

8-Methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (2.5 g, 0.0126 mole), prepared as described in Example 1, was reacted with 1.51 ml (0.0189 mole) ethyl chloroformate according to the procedure described above for 3-(N,N-diethylcarbamyl)-8-methyl-3,8-diazabicyclo[3.2.1]octane in Example 1. A white monohydrochloride, melting point 200°-205° C, was obtained in 73% yield: 2.16 g.

Sources & evidence

ORD record: ord-63b9733f09c8406cabd50b979f16d7b7
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03951980

Reaction notes

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