Carbon tetrabromide → (3R,4S)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine
Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([OH:16])[C@@H:13]([CH2:17]O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:19]=[N+:20]=[N-:21].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br>C(OCC)(=O)C.CO.ClCCl.CN(C)C=O>[N:19]([CH2:17][C@@H:13]1[C@H:14]([OH:16])[CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12]1)=[N+:20]=[N-:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 60 °C
Procedure
(3R,4S)-[1-Benzyloxycarbonyl-4-hydroxypyrrolidin-3-yl]methanol (2.33 g), sodium azide (1.81 g), triphenylphosphine (2.67 g), and N,N-dimethylformamide (46 mL) were mixed with one another. While this mixture was cooled on an ice bath, a dichloromethane solution (10 mL) of carbon tetrabromide (3.38 g) was added dropwise. The reaction mixture was stirred for 13 hours at room temperature and additional 3 hours at 60° C., followed by addition of methanol (3 mL) and concentration under reduced pressure. The resulting residue was dissolved in ethyl acetate (200 mL) and was washed with a saturated aqueous solution of sodium chloride (2×50 mL), followed by drying over anhydrous sodium sulfate and concentration under reduce pressure. The resulting residue was purified on a silica gel column (eluant=ethyl acetate:hexane=2:1) to give 2.18 g of (3R,4S)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine as a milky white syrup-like product.
Workup
- temperatureWhile this mixture was cooled on an ice bath
- washwas washed with a saturated aqueous solution of sodium chloride (2×50 mL)
- dry with materialby drying over anhydrous sodium sulfate and concentration
- customThe resulting residue was purified on a silica gel column (eluant=ethyl acetate:hexane=2:1)
Sources & evidence
- ORD record
- ord-31e579a49c9d4429a14cd7a32f3f78ed
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153851B2
Reaction notes
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