Triphenylphosphine → HCID 71544105, compound

HRID 240443Notes

Reaction equation

HRID 240443 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH2:17][CH2:16][N:15]3[CH2:18][C@@H:19]([OH:21])[CH2:20][C@@H:14]3[CH2:13]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[CH:24]1([C:27]2[N:28]=[CH:29][C:30](O)=[N:31][CH:32]=2)[CH2:26][CH2:25]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>O1CCCC1>[CH:24]1([C:27]2[N:28]=[CH:29][C:30]([O:21][C@H:19]3[CH2:18][N:15]4[CH2:16][CH2:17][N:12]([S:9]([C:5]5[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:22])([F:1])[F:23])[CH:4]=5)(=[O:11])=[O:10])[CH2:13][C@H:14]4[CH2:20]3)=[N:31][CH:32]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86680438HCID 86680438, compoundHCID 178516741HCID 178516741, compound

Product 1

HCID 71544105HCID 71544105, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (7S,8aR)-2-{[3-(trifluoromethyl)phenyl]sulfonyl}octahydropyrrolo[1,2-a]pyrazin-7-ol (Example 17, 103 mg, 0.294 mmol), 5-cyclopropylpyrazin-2-ol (40 mg, 0.294 mmol) and triphenylphosphine (154 mg, 0.588 mmol) in tetrahydrofuran (1 mL) was stirred at room temperature for 1 hour. Then (E)-diisopropyl diazene-1,2-dicarboxylate (119 mg, 0.588 mmol) was added, and the reaction was continued at room temperature overnight. The solution was concentrated, and the residue was purified by chromatography on silica gel (ethyl acetate/hexane=3:2) to give the title compound (68 mg, 48% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.86 (m, 4H), 1.22 (m, 2H), 2.12 (m, 4H), 2.41 (m, 2H), 3.01 (m, 2H), 3.67 (m, 1H), 3.83 (m, 1H), 5.25 (m, 1H), 7.94 (m, 1H), 8.03 (m, 1H), 8.15 (m, 4H); MS (ESI) m/z 469 (M+H)+.

Workup

  1. waitthe reaction was continued at room temperature overnight
  2. concentrationThe solution was concentrated
  3. customthe residue was purified by chromatography on silica gel (ethyl acetate/hexane=3:2)

Sources & evidence

ORD record
ord-8d1696369627434e9cdfd83320cf89e1
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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