Methylamine ethanol → tert-butyl (2S,3R)-3-hydroxy-4-(methylamino)-1-(tetrahydro-2H-pyran-4-yl)butan-2-ylcarbamate

HRID 253584Notes

Reaction equation

HRID 253584 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH:8]([CH:16]1[CH2:18][O:17]1)[CH2:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][NH2:21].CCO>>[OH:17][C@H:16]([CH2:18][NH:21][CH3:20])[C@@H:8]([NH:7][C:6](=[O:19])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 22028356Methylamine ethanolHCID 76605248[1-Oxiranyl-2-(tetrahydro-pyran-4-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 57786531tert-butyl (2S,3R)-3-hydroxy-4-(methylamino)-1-(tetrahydro-2H-pyran-4-yl)butan-2-ylcarbamate

Conditions

Temperature
35 °C

Procedure

A 250 mL flask was charged with [1-oxiranyl-2-(tetrahydro-pyran-4-yl)-ethyl]-carbamic acid tert-butyl ester (150 mg, 0.55 mmol) dissolved in MeNH2/EtOH solution and stirred overnight at 30-40° C. Then the mixture was concentrated and used directly in the next step.

Workup

  1. concentrationThen the mixture was concentrated

Sources & evidence

ORD record
ord-309c611308dd444d9a815a6ce47bffbb
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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