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

HRID 2058964Notes

Reaction equation

HRID 2058964 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-ac9f25ee10524407b783c27b78b6ec9a
Source dataset
uspto-grants-1982_03
Patent number
US04320137

Reaction notes

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