benzyl (3R,4R)-3-((tert-butoxycarbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate → (3R,4R)-(4-Hydroxy-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

HRID 539986Notes

Reaction equation

HRID 539986 reaction equation
C(OC([N:11]1[CH2:15][C@@H:14]([OH:16])[C@H:13]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>CO.O1CCCC1.[OH-].[Pd+2].[OH-]>[OH:16][C@@H:14]1[CH2:15][NH:11][CH2:12][C@H:13]1[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24]

Participants

6

Reactant 2

HCID 59640637benzyl (3R,4R)-3-((tert-butoxycarbonyl)amino)-4-hydroxypyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59640689(3R,4R)-(4-Hydroxy-pyrrolidin-3-yl)-carbamic acid tert-butyl esterYield 94%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-3-tert-butoxycarbonylamino-4-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester (3.9 g) in methanol (31 mL) and tetrahydrofuran (7 mL) was added palladium hydroxide (20 wt % Pd on carbon, 500 mg) and the mixture was stirred at room temperature under 40-45 psi of hydrogen atmosphere overnight. The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was triturated in the mixture of ethyl acetate and diisopropylether and filtered to remove the insoluable materials. The filtrate was concentrated in vacuo to afford 2.0 g of trans-tert-butyl [4-hydroxypyrrolidin-3-yl]carbamate (yield was 94%) as a powder. MS obsd. (ESI+) [(M+H)+] 203.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was triturated in the mixture of ethyl acetate and diisopropylether
  4. filtrationfiltered
  5. customto remove the insoluable materials
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b4cb7c71c3564e99aab13129df25f983
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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