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

HRID 1197827Notes

Reaction equation

HRID 1197827 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-88b53924938340f192c6abdcd9f47c09
Source dataset
uspto-grants-1994_01
Patent number
US05278170

Reaction notes

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