1,4-Bis(diphenylphosphino)butane → HCID 86598905, compound

HRID 456752Notes

Reaction equation

HRID 456752 reaction equation
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([OH:17])[CH2:14]2)[N:11]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:9])#[N:2].[C:25]1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)[CH:30]=CC=C[CH:26]=1.C(=O)(OCC)OCC=C>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH2:30]([O:17][C@H:13]1[C@H:12]2[CH2:16][C@H:15]([C@@H:10]([C:8]([N:4]3[CH2:5][CH2:6][CH2:7][C@H:3]3[C:1]#[N:2])=[O:9])[N:11]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1)[CH:25]=[CH2:26]

Participants

6

Reactant 3

HCID 821241,4-Bis(diphenylphosphino)butaneHCID 137020Allylethyl carbonateHCID 86598896tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 86598905HCID 86598905, compoundYield 715.2%

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 5-7 (510 mg) in tetrahydrofuran (5.0 mL), were added 1,4-bis(diphenylphosphino)butane (64.8 mg), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (39.3 mg) and allyl ethyl carbonate (0.4 mL). The mixture was stirred at 65° C. for 4 hrs. The resulting mixture was evaporated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate to give the target compound (408 mg).

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-979686a2bd8849ac9d0f8a5ad53e7b93
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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