Potassium Hydroxide → (1R)-2-(methylamino)-1-pyrazin-2-ylethanol

HRID 23709

Reaction equation

O1C=CC=C1[C@H](O)CNC.[CH3:11][N:12]1[CH2:16][C@H:15]([C:17]2[CH:22]=[N:21][CH:20]=[CH:19][N:18]=2)[O:14]C1=O.[OH-].[K+]>>[CH3:11][NH:12][CH2:16][C@H:15]([C:17]1[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1)[OH:14]

Participants

Reactant 3

HCID 14797Potassium Hydroxide

HCID 10214399(1R)-1-(2-furyl)-2-(methylamino)ethanol

HCID 69742350HCID 69742350, compound

Product 1

HCID 10285809(1R)-2-(methylamino)-1-pyrazin-2-ylethanolYield 79%

Procedure

As described for the preparation of (1R)-1-(2-furyl)-2-(methylamino)ethanol, the oxazolidinone (1.51 g, 8.43 mmol) is treated with 1N aq. KOH (42.1 mL, 5 equiv., 42.1 mmol ) to give (1R)-2-(methylamino)-1-pyrazin-2-ylethanol (1.02 g, 6.65 mmol) in 79% yield as a white solid. MP: 84-85° C.; Specific Rotation [α]D25+66 (c 0.94, methanol).

Sources & evidence

ORD record: ord-551598f4c36444969269f1c9883f2a71
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852731B2

Linked notes

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