Water → (2R,4R)-1-tert-butyl 2-methyl 4-azidopiperidine-1,2-dicarboxylate

HRID 1685457Notes

Reaction equation

HRID 1685457 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[C@H:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:12]([C:23]([O:25][CH3:26])=[O:24])[CH2:11]1)(=O)=O.O>CN(C=O)C>[N:1]([C@@H:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C@@H:12]([C:23]([O:25][CH3:26])=[O:24])[CH2:11]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 11151879HCID 11151879, compound

Product 1

HCID 54053444(2R,4R)-1-tert-butyl 2-methyl 4-azidopiperidine-1,2-dicarboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

NaN3 (15.8 g, 243 mmol) was added to a solution of (2R,4S)-1-tert-butyl 2-methyl 4-(methylsulfonyloxy)piperidine-1,2-dicarboxylate (26.7 g, 81 mmol) in dry DMF (100 mL). The mixture was heated at 60° C. for 18 hours. Water (300 mL) was added to the reaction mixture and extracted with ethyl acetate/heptane (2:1) (2×200 mL). The combined organic layer was washed by brine and dried over MgSO4, filtered and concentrated under reduced pressure to give a colorless oil 22.5 g (98%). LC-MS: 285.0 (t=2.5 min).

Workup

  1. extractionextracted with ethyl acetate/heptane (2:1) (2×200 mL)
  2. washThe combined organic layer was washed by brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c327649bf3814346a59d1e8c4f053460
Source dataset
uspto-grants-2012_04
Patent number
US08148401B2

Reaction notes

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