Sodium Azide → HCID 59201472, compound

HRID 451688Notes

Reaction equation

HRID 451688 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([O:23][CH2:24][CH2:25]OS(C)(=O)=O)[C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1.[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N:31]([CH2:25][CH2:24][O:23][CH:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[F:1])[C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1)=[N+:32]=[N-:33]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 59201345HCID 59201345, compound

Product 1

HCID 59201472HCID 59201472, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3R)-tert-butyl 3-((2,3-difluorophenyl)(2-(methylsulfonyloxy)ethoxy)methyl)piperidine-1-carboxylate (4.2 g, 9.4 mmol) and solid NaN3 (0.92 g, 14.1 mmol) in anhydrous DMF (30 mL) was heated to 80° C. overnight. The reaction mixture was cooled to rt and diluted with ethyl acetate (80 mL), the organic phase was washed with water (30 mL×3), dried over Na2SO4 and evaporated. The residue was separated on a silica column to give (3R)-tert-butyl 3-((2-azidoethoxy)(2,3-difluorophenyl)methyl)piperidine-1-carboxylate (3.4 g, 92%). 1H NMR (CDCl3, 400 MHz) δ 7.14 (m, 3H), 4.50 (q, 1H), 4.10 (m, 1H), 3.40 (m, 4H), 2.70 (m, 2H), 1.90 (m, 2H), 1.65 (m, 1H), 1.41 (d, 9H).

Workup

  1. washthe organic phase was washed with water (30 mL×3)
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue was separated on a silica column

Sources & evidence

ORD record
ord-18ca154d6c5e4ed58063465995270b05
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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