Sodium Hydroxide → Rasagiline

HRID 401852Notes

Reaction equation

HRID 401852 reaction equation
[C:1]1(S(OCC#C)(=O)=O)[CH:6]=CC=C[CH:2]=1.[NH2:14][CH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:2]#[C:1][CH2:6][NH:14][C@H:15]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 802732-Propyn-1-ol, 1-benzenesulfonateHCID 123445(+-)-1-Aminoindan

Product 1

HCID 3052776Rasagiline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

U.S. Pat. No. 5,532,415 discloses process for preparation of R(+)-Rasagiline mesylate which comprises treating a solution of propargyl benzenesulfonate (3) and racemic aminoindan (2) in toluene with aqueous solution of 15% sodium hydroxide to get racemic Rasagiline base (4). The obtained crude racemic Rasagiline is treated with L-tartaric acid in isopropanol (IPA) to get di(R-(+)-N-propargyl-1-aminoindan)-L-tartrate (5) which is recrystallized from 1:1 methanol/isopropanol. The obtained tartrate salt is reacted with methanesulphonic acid in isopropanol at reflux to obtain R(+)-Rasagiline mesylate. The disadvantage of this process is that the scheme consists of low atom efficiency and involves several steps to obtain the final product.

Sources & evidence

ORD record
ord-0bba4b190b374546a4df81e5fdfebfb8
Source dataset
uspto-grants-2014_06
Patent number
US08741962B2

Reaction notes

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