Sodium Azide → tert-butyl [(1R,2R)-2-azido-3,3-difluorocyclohexyl]carbamate

HRID 1895880Notes

Reaction equation

FC(F)(F)S(O[C@H:7]1[C@H:12]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH2:10][CH2:9][C:8]1([F:22])[F:21])(=O)=O.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[N:25]([C@H:7]1[C:8]([F:22])([F:21])[CH2:9][CH2:10][CH2:11][C@H:12]1[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N+:26]=[N-:27]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of (1S,6R)-6-[(tert-butoxycarbonyl)amino]-2,2-difluorocyclohexyl trifluoromethanesulfonate 26 (2.32 g, 6.05 mmol) and sodium azide (2.36 g, 36.3 mmol) in DMF was sealed and heated to 100° C. for 3 hours in a microwave reactor. The reaction was partitioned between water and ethyl acetate. The organics were washed with water, dried over magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (0-15% ethyl acetate in hexanes) gave 0.94 g (56%) of tert-butyl [(1R,2R)-2-azido-3,3-difluorocyclohexyl]carbamate 28 as a white solid: 1H NMR (500 MHz, CDCl3) δ 4.75 (1H, m), 3.98 (1H, bs), 3.88 (1H, bm), 1.96 (2H, m), 1.70 (2H, m), 1.46 (9H, s), 1.37 (2H, m).

Workup

customThe reaction was partitioned between water and ethyl acetate
washThe organics were washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated in vacuo
customPurification by flash chromatography (0-15% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-5313a8c1b9954d059a711e5c03768d31
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518911B2

Reaction notes

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