Magnesium → (2R,3S)-2-isopropyl-morpholine-3-carboxylic acid methyl ester

HRID 63689Notes

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:10]([CH:11]([CH3:13])[CH3:12])[O:9][CH2:8][CH2:7][N:6]1S(C1C=CC(C)=CC=1)(=O)=O)=[O:4].[Mg]>CO>[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:10]([CH:11]([CH3:13])[CH3:12])[O:9][CH2:8][CH2:7][NH:6]1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester (0.20 g, 0.59 mmol) and magnesium powder (70 mg, 2.9 mmol) in anhydrous methanol (5 mL) was stirred for 3 hours at 60° C. The solid was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue as crude product was used in next step without purification. MS: calc'd (MH+) 188, measured (MH+) 188.

Workup

customThe solid was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue as crude product was used in next step without purification

Sources & evidence

ORD record: ord-1048e16e85304f0ebd438a9bf419e7dc
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447086B2

Reaction notes

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