2-(Methylamino)ethanol → N-Cbz-N-methyl-2-aminoethanol

HRID 1634022Notes

Reaction equation

[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[CH2:6]([O:13][C:14](Cl)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[CH2:6]([O:13][C:14](=[O:15])[N:2]([CH2:3][CH2:4][OH:5])[CH3:1])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Reactant 2

HCID 80162-(Methylamino)ethanol

HCID 10387Benzyl chloroformate

Product 1

HCID 13279869N-Cbz-N-methyl-2-aminoethanol

Procedure

N-methylethanolamine was treated with benzylchloroformate to give (2-hydroxy- ethyl)-methyl-carbamic acid benzyl ester. The product was treated with methanesulfonyl chloride and Et3N in CH2Cl2 to give methanesulfonic acid 2-(benzyloxycarbonyl-methyl-amino)-ethyl ester. The resulting mesylate is used to alklylate 3 as described for the preparation of 4. The isopropenyl group is removed with acid as described for 6. The product is alkylated as described for compound 7 and the benzyloxy group was removed with catalytic hydrogenation (Pd/C) to give compound 99.

Sources & evidence

ORD record: ord-60e7791697ee495298f49d8117df4a4f
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506738B1

Reaction notes

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