Salicylic Acid → benzyl 3-(1H-tetrazol-5-yl)pyrrolidine-1-carboxylate

HRID 217439Notes

Reaction equation

[C:1]([CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4]1)#[N:2].[N-:18]=[N+:19]=[N-:20].[Na+].C(Cl)Cl.C(O)(=O)C1C(=CC=CC=1)O>C1(C)C=CC=CC=1>[NH:18]1[C:1]([CH:3]2[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:4]2)=[N:2][N:20]=[N:19]1

Participants

Conditions

Temperature: 115 °C

Procedure

To a solution of benzyl 3-cyanopyrrolidine-1-carboxylate (1.0 g) and TEA hydrochloride (2.99 g) in toluene was added sodium azide (1.41 g) at 25° C., followed by stirring at 115° C. for 5 hours. The reaction liquid was left to be cooled and DCM (10 mL) was added thereto. Then, to a 5% aqueous salicylic acid solution (100 mL) was added dropwise the reaction liquid, followed by stirring at 25° C. for 1 hour. The reaction liquid was extracted with EtOAc (30 mL) three times. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 80:20) to obtain benzyl 3-(1H-tetrazol-5-yl)pyrrolidine-1-carboxylate (10.8 g) as a colorless liquid.

Workup

customThe reaction liquid
waitwas left
temperatureto be cooled
customthe reaction liquid
stirringby stirring at 25° C. for 1 hour
customThe reaction liquid
extractionwas extracted with EtOAc (30 mL) three times
washThe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 80:20)

Sources & evidence

ORD record: ord-caf90f8cacf1436796a6cdc20495154f
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193378B2

Reaction notes

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