Dimethylformamide → HCID 59201594, compound

HRID 451722Notes

Reaction equation

HRID 451722 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:20]2[CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]2)([O:12][CH2:13][CH2:14]OS(C)(=O)=O)[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.CN(C=O)C.[N-:38]=[N+:39]=[N-:40].[Na+]>C(OCC)(=O)C.O>[N:38]([CH2:14][CH2:13][O:12][C@:8]([C@@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]1)([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:9][CH2:10][CH3:11])=[N+:39]=[N-:40]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 59201550HCID 59201550, compound

Product 1

HCID 59201594HCID 59201594, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

(R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(methylsulfonyloxy)ethoxy)butyl)piperidine-1-carboxylate (900 mg, 1.82 mmol) was dissolved into anhydrous DMF (15 mL), solid NaN3 (230 mg, 3.51 mmol) was added and the reaction mixture was heated to 70° C. overnight. The reaction mixture was cooled to rt and then was diluted with ethyl acetate (110 mL), and water (30 mL), the organic phase was washed with water (3×20 mL), dried over Na2SO4 and evaporated to give (R)-tert-butyl 3-((R)-1-(2-azidoethoxy)-1-(3-chlorophenyl)butyl)piperidine-1-carboxylate (790 mg, 99%).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to rt
  3. washthe organic phase was washed with water (3×20 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-6d6f932c036f480283df3ef0e1d013f6
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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