rac-benzyl (3R,4R)-3-hydroxy-4-phenoxypyrrolidine-1-carboxylate → Rac-(3r,4r)-4-phenoxypyrrolidin-3-ol

HRID 971682Notes

Reaction equation

HRID 971682 reaction equation
[OH:1][C@H:2]1[C@H:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][N:4](C(OCC2C=CC=CC=2)=O)[CH2:3]1>C(O)C.[Pd]>[OH:1][C@H:2]1[C@H:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][NH:4][CH2:3]1

Participants

4

Reactant 1

HCID 70546202rac-benzyl (3R,4R)-3-hydroxy-4-phenoxypyrrolidine-1-carboxylate

Product 1

HCID 13192209Rac-(3r,4r)-4-phenoxypyrrolidin-3-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

28.2 g (0.09 mol) of trans-3-hydroxy-4-phenoxy-1-carbobenzyloxy-pyrrolidine are dissolved in 280 ml of ethanol and hydrogenated in the presence of 3 g of a 5% strength palladium-on-charcoal catalyst under normal pressure and at room temperature. After the absorption of hydrogen has ceased, the catalyst is filtered off by means of diatomaceous earth and the filtrate is evaporated under a water pump vacuum. The residue is crystallised from methanol/ether and gives trans-3-hydroxy-4-phenoxy-pyrrolidine with a melting point of 120°-122°. The crystalline neutral fumarate with a melting point of 145°-146° is obtained by reacting the base with a solution of fumaric acid in methanol/ether.

Workup

  1. customAfter the absorption of hydrogen
  2. filtrationthe catalyst is filtered off by means of diatomaceous earth
  3. customthe filtrate is evaporated under a water pump vacuum
  4. customThe residue is crystallised from methanol/ether

Sources & evidence

ORD record
ord-04cf494ca0f5413bb503fd3e1245930a
Source dataset
uspto-grants-1979_07
Patent number
US04160837

Reaction notes

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