Triphenylphosphine → 3((1-BOC-2-(S)-pyrrolidinyl)methoxy)-5-trifluoromethylpyridine

HRID 1416630Notes

Reaction equation

HRID 1416630 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]([C:21]([F:24])([F:23])[F:22])[CH:20]=1.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([N:8]1[CH2:11][CH2:10][CH2:25][C@H:9]1[CH2:12][O:13][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10511797tert-butyl (2S)-2-(hydroxymethyl)azetidine-1-carboxylateHCID 229897075-(Trifluoromethyl)pyridin-3-ol

Product 1

HCID 213096653((1-BOC-2-(S)-pyrrolidinyl)methoxy)-5-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 333 mg (1.20 mmol) sample of 1-BOC-2-(S)-azetidinemethanol, prepared as in Example 7b above, and 230 mg (1.30 mmol) of 3-hydroxy-5-trifluoromethylpyridine, from step 66b above, were reacted with triphenylphosphine and DEAD (1.2 mmol each) in 5 mL of THF according to the procedure of Example 14a, to give 360 mg of the title compound. MS (D)CI/NH3) m/e 347 (M+H)+. 1H so NMR (CDCl3, 300 MHz) δ: 8.50 (s, 1H), 8.48 (s, 1H), 7.46 (s, 1H), 4.28-3.90 (m, 3H), 3.48-3.84 (m, 2H), 2.12-1.87 (m, 4H).

Sources & evidence

ORD record
ord-c5e027c3dec9468da59c43a29757ac20
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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