Tetrabutylammonium Fluoride → HCID 68611501, compound

HRID 2095304Notes

Reaction equation

HRID 2095304 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][C@@H:13]2[CH2:15][C@H:14]2[C:16]2[CH:17]=[N:18][CH:19]=[C:20]([O:22][CH2:23][C@@H:24]3[CH2:27][CH2:26][N:25]3[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:21]=2)(=O)=O)=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-:53]>C1COCC1>[C:31]([O:30][C:28]([N:25]1[CH2:26][CH2:27][C@H:24]1[CH2:23][O:22][C:20]1[CH:19]=[N:18][CH:17]=[C:16]([C@@H:14]2[CH2:15][C@H:13]2[CH2:12][CH2:11][F:53])[CH:21]=1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86642674HCID 86642674, compound

Product 1

HCID 68611501HCID 68611501, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the p-toluenesulfonate (237 mg, 0.47 mmol) and 5 mL of 1.0 M solution of n-Bu4NF in THF was stirred at room temperature for 10 h. The reaction mixture was concentrated in vacuo. The residue was purified by CC (SiO2, 50-60% EtOAc in hexane eluent) to give 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-[(1R,2S)-2-(2-fluoroethyl)cyclopropyl]pyridine as a viscous oil (160 mg, 97%). 1H NMR (CDCl3, 400 MHz) δ 8.14 (s, 1H), 8.06 (s, 1H), 6.84 (s, 1H), 4.78-4.51 (m, 3H), 4.37-4.22 (m, 1H), 4.11 (dd, J=10.1, 2.7 Hz), 3.87 (t, 2H, J=7.6 Hz), 2.36-2.21 (m, 2H), 1.75-1.66 (m, 3H), 1.42 (s, 9H), 1.12-0.96 (m, 1H), 0.95-0.82 (m, 2H). MS (ESI) m/z 351 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by CC (SiO2, 50-60% EtOAc in hexane eluent)

Sources & evidence

ORD record
ord-c39c6617ca2f4fbea72688939aa7c612
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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