Triphenylphosphine → tert-Butyl (2S,4S)-4-azido-2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate
Reaction equation
O[C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P([N:64]=[N+:65]=[N-:66])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[N:64]([C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:3]1)=[N+:65]=[N-:66]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred mixture of tert-butyl (2S,4R)-4-hydroxy-2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate (3.00 g, 11.6 mmol, step 2 of Example 9) in tetrahydrofuran (50 mL) were added triphenylphosphine (4.55 g, 17.4 mmol) and diethyl azodicarboxylate solution (50% in toluene, 7.56 mL, 17.36 mmol) at room temperature. After stirring for 15 min, diphenyl phosphoryl azide (3.74 mL, 17.36 mmol) was added to the mixture. The resulting mixture was stirred at room temperature for 40 h and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (4:1) to give 2.53 g (77%) of the title compound as a pale yellow oil.
Workup
- stirringThe resulting mixture was stirred at room temperature for 40 h
- concentrationconcentrated under reduced pressure
- customThe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (4:1)
Sources & evidence
- ORD record
- ord-4592049e5d974955b4761e7518787816
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906532B2
Reaction notes
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