Sodium Azide → tert-Butyl 4(S)-(2(S)-azidomethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 507832Notes

Reaction equation

CS(O[CH2:6][C@H:7]([CH:23]([CH3:25])[CH3:24])[CH2:8][C@H:9]1[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>CN1CCCN(C)C1=O>[N:26]([CH2:6][C@H:7]([CH:23]([CH3:25])[CH3:24])[CH2:8][C@H:9]1[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N+:27]=[N-:28]

Participants

Conditions

Temperature: 50 °C

Procedure

The mixture of 3.47 g of tert-butyl 4(S)-(2(S)-methanesulphonyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxyiate and 3.57 g of sodium azide in 50 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is stirred at 50° C. over 3 hours. The reaction mixture is cooled, poured onto water and extracted with diethyl ether (3×). The combined organic phases are washed successively with water (2×) and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a slightly yellowish oil. Rf=0.63 (1:1 EtOAc-heptane); Rt=5.86 (gradient I).

Workup

temperatureThe reaction mixture is cooled
additionpoured onto water
extractionextracted with diethyl ether (3×)
washThe combined organic phases are washed successively with water (2×) and brine
dry with materialdried over sodium sulphate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-1dd25da4b46f4613ae0bd8ebbeb3c7d5
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786307B2

Reaction notes

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