Triphenylphosphine → 3-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromo-6-chloropyridine

HRID 365839Notes

Reaction equation

HRID 365839 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]([N:39]1[CH2:42][CH2:41][C@H:40]1[CH2:43][OH:44])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[Br:45][C:46]1[CH:47]=[C:48](O)[CH:49]=[N:50][C:51]=1[Cl:52]>C1COCC1>[Br:45][C:46]1[CH:47]=[C:48]([O:44][CH2:43][C@@H:40]2[CH2:41][CH2:42][N:39]2[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:49]=[N:50][C:51]=1[Cl:52]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10511797tert-butyl (2S)-2-(hydroxymethyl)azetidine-1-carboxylateHCID 145952265-Bromo-6-chloropyridin-3-ol

Product 1

HCID 228726673-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromo-6-chloropyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl azodicarboxylate (1.52 mL, 9.6 mmol) in THF (56 mL) was added triphenylphosphine (2.52 g, 9.6 mmol) at 0° C., and the reaction mixture was stirred for half an hour. 1-BOC-2-(S)-azetidinemethanol (1.44 g, 7.7 mmol) and 5-bromo-6-chloropyridine-3-ol (1.4 g, 6.4 mmol; prepared according to V. Koch and S. Schnatterer, Synthesis 1990, 499-501)) were then added. The reaction mixture was slowly warmed up to room temperature overnight. Solvent was removed, and the residue was chromatographed on a silica gel column, eluting with CHCl3 :MeOH 100:1 to afford the title compound. MS (CI/NH3) m/z 377/379 (M+H)+.

Workup

  1. customSolvent was removed
  2. customthe residue was chromatographed on a silica gel column
  3. washeluting with CHCl3 :MeOH 100:1

Sources & evidence

ORD record
ord-d73efaef80d94b0785fbe4f5eb527995
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

Loading…