Methylamine → N-methyl-(3S)-3-hydroxy-3-(2-thienyl)propanamide

HRID 1988126Notes

Reaction equation

HRID 1988126 reaction equation
[OH:1][C@H:2]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[CH2:3][C:4](OC)=[O:5].[CH3:13][NH2:14]>>[CH3:13][NH:14][C:4](=[O:5])[CH2:3][C@H:2]([OH:1])[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 10397541methyl (3S)-3-hydroxy-3-(thiophen-2-yl)propanoate

Product 1

HCID 10261821N-methyl-(3S)-3-hydroxy-3-(2-thienyl)propanamide

Conditions

Temperature
60 °C

Procedure

23 g of methyl (3S)-3-hydroxy-3-(2-thienyl)propanoate from experiments described in the Examples 1 and [lacuna] were initially introduced, and 130 ml of a 2-molar methanolic solution of methylamine were added. This mixture is stirred at 60° C. for 4 h, cooled and then concentrated in vacuo. 24 g (purity 87%; 90% of theory) are obtained in this way. The crude product can be used as such for the next step or else recrystallized from methylene chloride and hexane. This yielded 18 g of N-methyl-(3S)-3-hydroxy-3-(2-thienyl)propanamide (75% of theory) in the form of white crystals.

Workup

  1. additionwere initially introduced
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. custom24 g (purity 87%; 90% of theory) are obtained in this way
  5. customelse recrystallized from methylene chloride and hexane

Sources & evidence

ORD record
ord-70dbaf1969a84857999a26627bcb56ec
Source dataset
uspto-grants-2009_06
Patent number
US07553970B2

Reaction notes

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