Triphenylphosphine → HCID 25182421, compound

HRID 2037419Notes

Reaction equation

HRID 2037419 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])[CH:16]=[CH:17][CH:18]=2)[CH2:8][CH2:7]1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[NH2:1][CH2:4][CH2:5][C:6]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])[CH:16]=[CH:17][CH:18]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 59532362HCID 59532362, compound

Product 1

HCID 25182421HCID 25182421, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 6-(2-azidoethyl)-3-(2′,4′-difluorobiphenyl-3-yl)-6-phenyl-1,3-oxazinan-2-one (100 mg, 0.23 mmol) in 20:1 THF/H2O (3 mL) was added PPh3 (72 mg, 0.28 mmol). The reaction mixture was stirred at rt overnight. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel to afford 6-(2-aminoethyl)-3-(2′,4′-difluorobiphenyl-3-yl)-6-phenyl-1,3-oxazinan-2-one (30 mg, 31%). 1H NMR (400 MHz, CDCl3): δ=2.20-2.51 (m, 2H), 2.51-2.60 (m, 2H), 2.72 (m, 1H), 3.00 (m, 1H), 3.24 (m, 1H), 3.53 (m, 1H), 6.85-6.99 (m, 2H), 7.14 (m, 1H), 7.31-7.50 (m, 8H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-406a4ddc470b42a3b1a1fda1117c005f
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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