Sodium Iodide → (s)-Tert-butyl 2-(azidomethyl)morpholine-4-carboxylate

HRID 1478555Notes

Reaction equation

S(O[CH2:12][C@H:13]1[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1)(C1C=CC(C)=CC=1)(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+].[Na+].[I-]>CN(C=O)C>[N:26]([CH2:12][C@H:13]1[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1)=[N+:27]=[N-:28]

Participants

Conditions

Temperature: 70 °C

Procedure

(S)-tert-butyl 2-((tosyloxy)methyl)morpholine-4-carboxylate (63.7 g, 171.52 mmol) was dissolved in DMF (550 ml), and then NaN3 (44.59 g, 686.08 mmol) and NaI (2.5 g, 17.15 mmol) were added, followed by stirring at 70° C. overnight. After the completion of the reaction, the reaction mixture was extracted with H2O and EA, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (EA:Hex=1:5), to give (S)-tert-butyl 2-(azidomethyl)morpholine-4-carboxylate as a white solid (31.1 g, 75%).

Workup

customAfter the completion of the reaction
extractionthe reaction mixture was extracted with H2O and EA
customby drying
filtration(Na2SO4), filtration, and concentration under reduced pressure
customthe residue was purified by column chromatography (EA:Hex=1:5)

Sources & evidence

ORD record: ord-9bc23409486449f08e42b016e3e4a52e
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403831B2

Reaction notes

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