Methanesulfonyl chloride → Tert-butyl 2-(((methylsulfonyl)oxy)methyl)morpholine-4-carboxylate

HRID 1505679Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][O:16][CH:15]([CH2:19][OH:20])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>C(Cl)Cl>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][O:16][CH:15]([CH2:19][O:20][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Methane sulfonyl chloride (71 μl; 0.92 mmol; 1.0 eq.) was added to a solution of 2-hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester (200 mg; 0.92 mmol; 1.0 eq.) and TEA (190 uL; 1.38 mmol; 1.5 eq.) in anhydrous DCM (3 mL) maintained at 0° C. and under nitrogen atmosphere. The reaction mixture was stirred at RT O/N. The reaction mixture was washed with 10% citric acid solution and brine. Organic phase was dried over magnesium sulfate, filtered and concentrated to give the title compound as a brown oil (250 mg, 92%). 1H NMR (300 MHz, DMSO) δ 4.33-4.13 (m, 2H), 3.91-3.78 (m, 2H), 3.75-3.55 (m, 4H), 3.42 (td, J=11.6, 2.8 Hz, 1H), 3.20 (s, 3H), 1.41 (s, 9H).

Workup

washThe reaction mixture was washed with 10% citric acid solution and brine
dry with materialOrganic phase was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-a957f7ade0d749de8feb093e362280a1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216991B2

Reaction notes

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