Methanol → Methyl 1-amino-1-cyclopentanecarboxylate, HCl
Reaction equation
CO.S(Cl)([Cl:5])=O.[NH2:7][C:8]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:16]COCC>CC(C)=O>[ClH:5].[CH3:16][O:14][C:13]([C:8]1([NH2:7])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Preparation of methyl-1-N,N-dichloroamino-1-cyclopentanecarboxylate: To 30 ml of absolute methanol at 0° C, there was added dropwise with stirring over 0.5 hr. 7.9 ml of freshly distilled thionyl chloride. When the addition of thionyl chloride was completed, 12.9 g (0.1 mol) 1-amino-1-cyclopentanecarboxylic acid was added in portions over 0.25 hr. The suspension was heated with stirring, and the temperature maintained at 75° C for 2.5 hr. after solution of the reaction suspension. Removal of the methanol under reduced pressure gave an off-white crystalline mass. Trituration of this material with anhydrous ether gave 16.1 g (0.09 mol), 90%, methyl-1-amino-1-cyclopentanecarboxylate hydrochloride, mp 205°- 207° C acetone:hexane, kr (KBr) 1740 (C=O) cm-1 ; pmr (D2O) δ 3.95 (S, 3H) and 2.83 - 1.66 (m, 8H) ppm.
Workup
- temperatureThe suspension was heated
- stirringwith stirring
- customRemoval of the methanol under reduced pressure
- customgave an off-white crystalline mass
Sources & evidence
- ORD record
- ord-7d88244d09994006a81b72b0b749d5d1
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03966796
Reaction notes
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