Triphenylphosphine → (R)-3-((R)-2-Cyclopentyl-2-hydroxy-2-phenylacetoxy)pyrrolidine-1-carboxylic acid t-butyl ester

HRID 884829Notes

Reaction equation

HRID 884829 reaction equation
[CH:1]1([C@@:6]([OH:16])([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][C@H:26](O)[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][C@@H:26]([O:8][C:7](=[O:9])[C@:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)([OH:16])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylateHCID 948620alpha-Cyclopentylmandelic acid, (+)-

Product 1

HCID 57613514(R)-3-((R)-2-Cyclopentyl-2-hydroxy-2-phenylacetoxy)pyrrolidine-1-carboxylic acid t-butyl esterYield 282.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-Cyclopentylhydroxyphenylacetic acid (20 g, 90.8 mmol), (S)-3-hydroxypyrrolidine-1-carboxylic acid t-butyl ester (18 g, 96.2 mmol) and triphenylphosphine (24 g, 91.5 mmol) were dissolved in THF (100 mL). Diisopropyl azodicarboxylate (19.7 mL, 99.9 mmol) was added slowly at room temperature. The mixture was stirred overnight at room temperature. The solvent was removed by rotary evaporation. EtOAc was then added and the solution was washed with a saturated NaHCO3 solution, then saturated aqueous NaCl. The organic layer was dried over Na2SO4 then concentrated to yield approximately 100 g of crude title compound, which was used immediately without further purification.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. additionEtOAc was then added
  3. washthe solution was washed with a saturated NaHCO3 solution
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationthen concentrated

Sources & evidence

ORD record
ord-41c0258845b245d9b6c439e81896169c
Source dataset
uspto-grants-2012_08
Patent number
US08242138B2

Reaction notes

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