Dimethylformamide → HCID 118007383, compound
Reaction equation
[CH3:1][C@H:2]1[CH2:7][C@@H:6](COS(C2C=CC(C)=CC=2)(=O)=O)[CH2:5][N:4]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:3]1.[N-:27]=[N+:28]=[N-:29].[Na+].CN(C=[O:35])C>CCOC(C)=O>[N:27]([CH2:7][C@@H:6]1[O:35][C@H:2]([CH3:1])[CH2:3][N:4]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:5]1)=[N+:28]=[N-:29]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of (3S,5R)-tert-butyl 3-methyl-5-((tosyloxy)methyl)piperidine-1-carboxylate (0.860 g, 2.232 mmol) in DMF (7 mL) at rt was added sodium azide (0.218 g, 3.347 mmol) after which time the reaction was warmed to 80° C. and stirred an additional 3 h. The completed reaction was cooled to rt, diluted with EtOAc (25 mL) and washed three times with water (5 mL each). The resultant organic layer was dried over anhydrous Na2SO4, filtered, concentrated after which time the crude product was purified over silica gel (Biotage eluting with 0 to 15% EtOAc in heptane gradient) to provide (2R,6R)-tert-butyl 2-(azidomethyl)-6-methylmorpholine-4-carboxylate, 37 (0.545 g, 2.126 mmol, 95.3% yield) as a colorless crystalline solid after concentration of the desired combined fractions and drying in vacuo.
Workup
- customThe completed reaction
- temperaturewas cooled to rt
- washwashed three times with water (5 mL each)
- dry with materialThe resultant organic layer was dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated after which time the crude product
- customwas purified over silica gel (Biotage eluting with 0 to 15% EtOAc in heptane gradient)
Sources & evidence
- ORD record
- ord-3b63e05f44854546912f43e3d6ff9d7b
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428495B2
Reaction notes
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