Triphenylphosphine → 3-(1-BOC-2-(R)-pyrrolidinylmethoxy)-5-trifluoromethylpyridine

HRID 617339Notes

Reaction equation

HRID 617339 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:16]1[CH:17]=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 688279N-(tert-Butoxycarbonyl)-D-prolinolHCID 5462977Diethyl azodicarboxylateHCID 229897075-(Trifluoromethyl)pyridin-3-ol

Product 1

HCID 213096603-(1-BOC-2-(R)-pyrrolidinylmethoxy)-5-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 332.9. mg (1.56 mmol) sample of (R)-1-t-butoxycarbonyl-2-pyrrolidinemethanol and 224.9 mg (1.30 mmol) of 3-hydroxy-5-trifluoromethylpyridine were reacted with triphenylphosphine and DEAD (1.56 mmol each) in 5 mL of THF according to the procedure of Example 14a, to give 386 mg of the title compound. MS (DCI/NH3) m/e 347 (M+H)+. 1H 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), 1.47 (s, 9H).

Sources & evidence

ORD record
ord-63765be499bb4283bb25dc2c8aa4c6fe
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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