benzyl tert-butyl ((1S,3S)-cyclopentane-1,3-diyl)dicarbamate → tert-Butyl N-((1S,3S)-3-aminocyclopentyl)carbamate

HRID 271389Notes

Reaction equation

HRID 271389 reaction equation
[C@H:1]1([NH:14]C(=O)OCC2C=CC=CC=2)[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1>CCO.[Pd]>[NH2:14][C@H:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:10])[CH3:12])[CH2:2]1

Participants

4

Reactant 1

HCID 59834942benzyl tert-butyl ((1S,3S)-cyclopentane-1,3-diyl)dicarbamate

Product 1

HCID 45091937tert-Butyl N-((1S,3S)-3-aminocyclopentyl)carbamateYield 113.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl tert-butyl (1S,3S)-cyclopentane-1,3-diylbiscarbamate (2.02 g, 6.04 mmol) and 10% Pd/C (142 mg) in EtOH (200 mL) was shaken on a Parr apparatus under hydrogen (36 psi) for 1 hr. The reaction mixture was filtered through celite and concentrated to give the title compound (1.37 g) as an opaque paste.

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5675fd6cfbd943378a1e41a4b3363bb7
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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