Triphenylphosphine → HCID 15927503, compound

HRID 1896213Notes

Reaction equation

HRID 1896213 reaction equation
O[C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16]C)=[O:15])[CH2:3]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[O:15]=[C:14]1[CH:4]2[CH2:3][CH:2]([CH2:6][N:5]2[C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[O:16]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 15927503HCID 15927503, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-tert-butyl 2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate (170.0 g, 0.736 mol) and PPh3 (237.0 g, 0.88 mol) in dry THF (1.5 L) was added dropwise DIAD (178.35 g, 0.88 mol) at 0° C. under N2 gas. After addition, the resulting reaction mixture was stirred at room temperature overnight. TLC (petroleum ether/EtOAc 3:1) indicated the complete consumption of compound 1A. The solvent was removed in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether/EtOAc 6:1) which gave the title compound IVa as a white solid (110.0 g, yield: 72.0%).

Workup

  1. additionAfter addition
  2. customthe resulting reaction mixture
  3. customthe complete consumption of compound 1A
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by column chromatography (silica gel, petroleum ether/EtOAc 6:1) which

Sources & evidence

ORD record
ord-23a995ed7e734a0796e1bde5b1a17d7b
Source dataset
uspto-grants-2013_08
Patent number
US08518952B2

Reaction notes

Loading…