trans-Benzyl 3-(tert-butoxycarbonylamino)-4-fluoropyrrolidine-1-carboxylate → tert-Butyl ((3R,4R)-4-fluoropyrrolidin-3-yl)carbamate

HRID 928195Notes

Reaction equation

HRID 928195 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:13]([F:14])[CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[F:14][C@@H:13]1[CH2:12][NH:11][CH2:10][C@H:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 118084929trans-Benzyl 3-(tert-butoxycarbonylamino)-4-fluoropyrrolidine-1-carboxylate

Product 1

HCID 58006941tert-Butyl ((3R,4R)-4-fluoropyrrolidin-3-yl)carbamateYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3R,4R)-benzyl 3-((tert-butoxycarbonyl)amino)-4-fluoropyrrolidine-1-carboxylate (3.0 g, 8.8 mmol) in MeOH (50 mL) was added wet Pd/C (0.3 g, 10%) under nitrogen. The suspension was degassed under vacuum and purged with hydrogen three times. The resulting mixture was stirred at rt under hydrogen balloon for 3 hr. The reaction mixture was filtered and the filtrate was concentrated to afford the title compound (1.6 g, 88% yield) as light yellow oil that solidified on standing.

Workup

  1. customThe suspension was degassed under vacuum
  2. custompurged with hydrogen three times
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9c708ef449754d64962de28bb1b2c5b6
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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