Triphenylphosphine → HCID 86715085, compound

HRID 533898Notes

Reaction equation

HRID 533898 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7].[CH:8]1([CH2:11][CH2:12][O:13][C:14]2[N:19]=[CH:18][C:17](O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(Cl)Cl>[CH:8]1([CH2:11][CH2:12][O:13][C:14]2[N:19]=[CH:18][C:17]([O:1][C@@H:2]3[CH2:6][CH2:5][NH:4][C:3]3=[O:7])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11029774(3S)-3-hydroxypyrrolidin-2-oneHCID 867150916-(2-Cyclopropyl-ethoxy)-pyridin-3-ol

Product 1

HCID 86715085HCID 86715085, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-3-hydroxy-pyrrolidin-2-one (0.79 g), 6-(2-cyclopropyl-ethoxy)-pyridin-3-ol (1.4 g), triphenylphosphine (2.25 g), DCM (30 mL) and THF (20 mL) was added DIAD (1.74 g). After 2 days the mixture was filtered and the filtrate was evaporated. The residue was purified by SGC (eluent: EA/MeOH 9:1) to provide the title compound. MS ESI+: m/z=263 [M+H]+.

Workup

  1. filtrationAfter 2 days the mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by SGC (eluent: EA/MeOH 9:1)

Sources & evidence

ORD record
ord-c36561a6174d4d1ab08e9242f8ae3283
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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