Benzylamine → Methyl 2-benzylisoindoline-5-carboxylate

HRID 1952985Notes

Reaction equation

HRID 1952985 reaction equation
NC([N:4]1C[C:11]2[C:6](=[CH:7][CH:8]=[C:9](CN)[CH:10]=2)[CH2:5]1)=O.Br[CH2:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1[CH2:27]Br)[C:20]([O:22][CH3:23])=[O:21].CC1C=C(C=CC=1C)C(OC)=O.C(N)C1C=CC=CC=1>>[C:6]1([CH2:5][N:4]2[CH2:16][C:17]3[C:26](=[CH:25][CH:24]=[C:19]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=3)[CH2:27]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 7504BenzylamineHCID 520902Methyl 3,4-dimethylbenzoateHCID 2736819Methyl 3,4-bis(bromomethyl)benzoateHCID 23301770HCID 23301770, compound

Product 1

HCID 23301778Methyl 2-benzylisoindoline-5-carboxylate

Procedure

The [2-(aminocarbonyl)-2,3-dihydro-1H-isoindol-5-yl]methanamine of general formula III may be prepared as follows, for example: The methyl 3,4-bis-(bromomethyl)benzoate obtainable in situ from methyl 3,4-dimethylbenzoate by photobromination, on being reacted with benzylamine, yields methyl 2,3-dihydro-2-(phenyl-methyl)-1H-isoindol-5-carboxylate, the ester function of which is converted in the usual way into a carboxamide function and then, by reduction with lithium aluminium hydride, into an aminomethyl function; the primary amino group is protected with a tert.butoxycarbonyl group, the benzyl group in the 2-position is removed by hydrogenolysis and replaced by an aminocarbonyl group, e.g. by treating the hydrochloride of the resulting 5-[[(tert.butoxycarbonyl)amino]methyl]-2,3-dihydro-1H-isoindole with sodium cyanate; removal of the tert.butoxycarbonyl protecting group, e.g. with methanolic hydrogen chloride solution, then yields the desired 2-(amino-carbonyl)-2,3-dihydro-1H-isoindol-5-yl]methanamine in the form of the hydrochloride.

Sources & evidence

ORD record
ord-d4a943e620ed422b860bc9e64cd93147
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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