Benzyl 2,5-dioxopyrrolidine-1-carboxylate → trans-Benzyl 3-hydroxycyclopentylcarbamate

HRID 271370Notes

Reaction equation

HRID 271370 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH2:7])[CH2:3]1.[CH2:8]([O:15][C:16](N1C(=O)CCC1=O)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[OH:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:16](=[O:17])[O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 3826287Benzyl 2,5-dioxopyrrolidine-1-carboxylateHCID 42614395(1S,3S)-3-Aminocyclopentan-1-ol

Product 1

HCID 59834849trans-Benzyl 3-hydroxycyclopentylcarbamateYield 981.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of crude trans-3-hydroxycyclopentanamine (0.42 g, 4.2 mmol) and N-(benzyloxycarbonyl)succinimide (1.05 g, 0.42 mmol) in acetonitrile (40 ml) was stirred at ambient temperature under nitrogen for 18 hours. The mixture was concentrated under reduced pressure. The residue was taken up in ethyl acetate (150 ml), washed with water (3×75 ml), and brine (50 ml), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure to give benzyl (trans-3-hydroxycyclopentyl)carbamate (0.97 g, 98%), as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washwashed with water (3×75 ml), and brine (50 ml)
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-fb46d788fc814cb2ad333ca1dcf47da3
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

Loading…