5-nitropyridin-3-ol → HCID 21345209, compound

HRID 367109Notes

Reaction equation

HRID 367109 reaction equation
[C:1]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][OH:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[C:15]1[CH:16]=[N:17][CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1>>[N+:21]([C:19]1[CH:20]=[C:15]([O:13][CH2:12][C@@H:9]2[CH2:10][CH2:11][N:8]2[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH:16]=[N:17][CH:18]=1)([O-:23])=[O:22]

Participants

3

Reactant 2

HCID 27629055-nitropyridin-3-olHCID 10511797tert-butyl (2S)-2-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 21345209HCID 21345209, compoundYield 73%

Procedure

1-BOC-2-(S)-azetidinylmethanol (868 mg, 4.64 mmol) and 3-hydroxy-5-nitropyridine from Example 132d (500 mg, 3.57 mmol) were coupled according the procedure of Example 17a. Solvent was removed, and the residue was chromatographed (silica gel, hexane/ethyl acetate, 5:1) to afford the title compound (800 mg, 73%). 1H NMR (CHCl3, 300 MHz) δ 1.45 (s, 9H), 2.56 (m, 2H), 4.52 (m, 4H), 4.82 (m, 1H), 8.25 (t, J=3 Hz, 1H), 8.65 (d, J=3 Hz, 1H), 9.05 (d, J=3 Hz, 1H). MS (DCI/NH3) m/z 310 (M+H)+.

Workup

  1. customSolvent was removed
  2. customthe residue was chromatographed (silica gel, hexane/ethyl acetate, 5:1)

Sources & evidence

ORD record
ord-24e7b17c5d024e06abb1e056801efc3a
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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