HCID 57971607, compound → Cyclopentyl O-Tert-Butyl-L-Serinate

HRID 548212Notes

Reaction equation

HRID 548212 reaction equation
[CH:1]1([O:6][C:7](=[O:26])[C@@H:8]([NH:15]C(OCC2C=CC=CC=2)=O)[CH2:9][O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:5][CH2:4][CH2:3][CH2:2]1>CCO.[OH-].[Pd+2].[OH-]>[CH:1]1([O:6][C:7](=[O:26])[C@@H:8]([NH2:15])[CH2:9][O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 57971607HCID 57971607, compound

Product 1

HCID 54280292Cyclopentyl O-Tert-Butyl-L-SerinateYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionic acid cyclopentyl ester (3.82 g, 0.011 mol) was dissolved in EtOH (50 ml). 20% wt. Palladium hydroxide (wet) was added cautiously to the solution. The system was evacuated and put under a hydrogen atmosphere for 4 hours. The system was evacuated and the palladium residues filtered off through Celite. The Celite was thoroughly washed with EtOH (3×5 ml). The solvent of the filtrate was removed in vacuo to give the product as a colourless oil (2.41 g, 100% yield). 1H NMR (300 MHz, CDCl3), δ: 1.15 (9H, s, CH3×3), 1.50-1.90 (10H, m, CH2×4, NH2), 3.50-3.70 (3H, m, CH2, CH), 5.22 (1H, s, CH).

Workup

  1. customThe system was evacuated
  2. customThe system was evacuated
  3. filtrationthe palladium residues filtered off through Celite
  4. washThe Celite was thoroughly washed with EtOH (3×5 ml)
  5. customThe solvent of the filtrate was removed in vacuo

Sources & evidence

ORD record
ord-af2bc64ae0724da48ef80debb1e95b9a
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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