O-Methylhydroxylamine hydrochloride → 1-Azabicyclo[2.2.1]hept-4-yl-N-methoxycarboxamide

HRID 2257419Notes

Reaction equation

HRID 2257419 reaction equation
Br.[N:2]12[CH2:8][C:5]([C:9]([O:11]CC)=O)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.Cl.[O:15]([NH2:17])[CH3:16]>C(N(CC)CC)C>[N:2]12[CH2:8][C:5]([C:9]([NH:17][O:15][CH3:16])=[O:11])([CH2:4][CH2:3]1)[CH2:6][CH2:7]2

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 22922786Ethyl 1-azabicyclo[2.2.1]heptane-4-carboxylate hydrobromide

Product 1

HCID 105832851-Azabicyclo[2.2.1]hept-4-yl-N-methoxycarboxamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Ethyl 1 -azabicyclo[2.2.1]hept-4-ylcarboxylate hydrobromide salt (D17, 16.85 g, 0.067 mole) was converted to the acid chloride hydrochloride salt and treated with methoxylamine hydrochloride (6.19 g, 0.074 mole) and triethylamine as in the method of Description 8 to give the title compound (D18) as a pale brown crystalline solid (4.60 g, 40%) m.p. 129°-134° C.

Sources & evidence

ORD record
ord-b2c4f3202cdd476dae6563db48ca0eb4
Source dataset
uspto-grants-1997_08
Patent number
USRE035593

Reaction notes

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