1-Benzylpyrrolidin-3-yl methanesulfonate → 2-[1-(Phenylmethyl)-3-pyrrolidinyl]-2H-tetrazole

HRID 1743005Notes

Reaction equation

[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[C-:22]=[N:21][N:20]=[N:19]1.[Na+]>CN(C)C=O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:19]2[N:20]=[N:21][CH:22]=[N:18]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 87.5 °C

Procedure

A suspension of N-benzyl-3-[(methylsulphonyl)oxy]pyrrolidine (2.2 g, 9.37 mmol) and sodium 1,2,3,4-tetrazolide (1.8 g, 19.6 mmol) in 50 ml of dimethylformamide was heated at 85-90° C. overnight. The reaction mixture was worked up the same as described in Example U. The crude product was purified over silica gel using hexane, ether and ethyl acetate as eluant to afford in order of elution 0.413 g of N-benzyl-3-(1,2,3,4-tetrazol-2-yl) pyrrolidine as an oil. 1H NMR (CDCl3) δ: 8.51 (s, 1H), 7.37-7.17 (m, 5H), 5.51-5.35 (m, 1H), 3.8-3.65 (q, 2H), 3.3-2.4 (m, 6H); and.26 g of N-benzyl-3-(1,2,3,4-tetrazol-1-yl)pyrrolidine as an oil. 1H NMR (CDCl3) 6 : 8.88 (s, 1H), 7.4-7.2 (m, 5H), 5.35-5.2 (m, 1H), 3.83-3.6 (q, 2 H), 3.2-2.3 (m, 5H), 2.15-2.00 (m, 1H).

Workup

customThe crude product was purified over silica gel

Sources & evidence

ORD record: ord-3b2dc642223e4600b9448398e0f1be9b
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05342846

Reaction notes

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