Dichloromethane → tert-Butyl 3-aminopropanoate

HRID 987561

Reaction equation

HRID 987561 reaction equation
[C:1](NCCCl)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:12][CH2:13][N:14](CC)CC.C(Cl)Cl>CN(C=O)C>[C:1]([CH2:12][CH2:13][NH2:14])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 3795708N-Boc-2-chloroethylamine

Product 1

HCID 4192171tert-Butyl 3-aminopropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compounds of formula IX may be prepared according to Scheme V. Alkylation of the secondary amine in a compound of formula VII or formula VIIa with 2-(N-Boc amino)ethyl chloride (prepared according to the procedure of Tanaka (Chem. Pharm. Bull. 1988, 36, 3125) in the presence of Et3N in a solvent such as CH2Cl2 or DMF gives the N-Boc ethylamine derivative of formula XI. Removal of the Boc group is accomplished by treatment with TFA in a solvent such as CH2Cl2 to give naphthyl-8-azabicyclo[3.2.1]octene/naphthyl-8-azabicyclo[3.2.1]octane of formula IX.

Sources & evidence

ORD record
ord-883014dee98d445abff8f5c4358c26d8
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Linked notes

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