Triethylamine → (3S,4S)-N-Cbz-3-azido-4-hydroxypyrrolidine
Reaction equation
[C:1]([N:8]1[CH2:12][C@H:11]([OH:13])[C@@H:10]([N:14]=[N+:15]=[N-:16])[CH2:9]1)([O:3][C:4]([CH3:7])(C)C)=[O:2].C(OCC)(=O)C.C(N(CC)CC)C.[CH:30]1[CH:35]=[CH:34]C(COC(Cl)=O)=[CH:32][CH:31]=1>FC(F)(F)C(O)=O.CCCCCC>[C:1]([N:8]1[CH2:12][C@H:11]([OH:13])[C@@H:10]([N:14]=[N+:15]=[N-:16])[CH2:9]1)([O:3][CH2:4][C:7]1[CH:34]=[CH:35][CH:30]=[CH:31][CH:32]=1)=[O:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A sample of the (3S,4S)—N-Boc-3-azido-4-hydroxypyrrolidine (80 mg, 0.35 mmol) was dissolved in trifluoroacetic acid (1 mL) and was stirred until no starting material was detected on TLC (25% ethyl acetate in hexane). The solution was evaporated under reduce pressure and the residue was dissolved in CH2Cl2 (2 mL). The solution was cooled to 0° C., triethylamine (117 μL, 0.84 mmol) and Cbz-Cl (60 mg, 0.35 mmol) were added, and the resulting solution was stirred for 2 hr at room temperature. The reaction mixture was washed with water, dried over Na2SO4, and evaporated. The residue was purified by flash chromatography (25% ethyl acetate in hexane) to give (3S,4S)—N-Cbz-3-azido-4-hydroxypyrrolidine (89 mg, 97%): [α]20D=+ 16.1° (c=1.00, CHCl3). Lit. [Kamal, A.; Shaik, A. A.; Sandbhor, M.; Malik, M. S.; Kaga, H. Tetrahedron Lett. 2004, 45, 8057-8059] for (3S,4S)—N-Cbz-3-azido-4-hydroxypyrrolidine: [0]25D=+14.3° (c=1.06, CHCl3).
Workup
- customThe solution was evaporated
- dissolutionthe residue was dissolved in CH2Cl2 (2 mL)
- stirringthe resulting solution was stirred for 2 hr at room temperature
- washThe reaction mixture was washed with water
- dry with materialdried over Na2SO4
- customevaporated
- customThe residue was purified by flash chromatography (25% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-f855899d69914358a06de3124ca30963
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404866B2
Reaction notes
Loading…