(2R)-2-(2-carbazol-9-yl-2-oxo-ethyl)-pentanoic Acid Benzyl Ester → (2R)-2-(2-carbazol-9-yl-2-oxo-ethyl)-pentanoic acid

HRID 491973Notes

Reaction equation

HRID 491973 reaction equation
C([O:8][C:9](=[O:30])[C@@H:10]([CH2:14][C:15]([N:17]1[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH2:11][CH2:12][CH3:13])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH:28]1[C:29]2[N:17]([C:15](=[O:16])[CH2:14][C@@H:10]([CH2:11][CH2:12][CH3:13])[C:9]([OH:30])=[O:8])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]=2[CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 57418778(2R)-2-(2-carbazol-9-yl-2-oxo-ethyl)-pentanoic Acid Benzyl Ester

Product 1

HCID 57418779(2R)-2-(2-carbazol-9-yl-2-oxo-ethyl)-pentanoic acidYield 84.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of (2R)-2-(2-carbazol-9-yl-2-oxo-ethyl)-pentanoic acid benzyl ester (4.50 g, 11.26 mmol) in EtOAc (60 ml) was treated with 10% Pd on carbon (˜400 mg) and the reaction mixture was then placed under an atmosphere of hydrogen. After 1 h further 10% Pd on carbon (−300 mg) was added and the reaction mixture was placed under hydrogen, with stirring, for a further 3 h after which the reaction mixture was filtered through a celite pad and concentrated to give the sub-title compound (2.94 g, 84%) as a white solid which also contained carbazole: 1H NMR (400 MHz, CDCl3) δ 0.92-1.04 (3H, m), 1.32-2.00 (4H, m), 3.19-3.34 (2H, m), 3.58-3.70 (1H, m), 7.30-7.53 (4H, m), 8.00-8.30 (4H, m).

Workup

  1. filtrationwas filtered through a celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-edea8ef4347541c290355292f1ffe1ac
Source dataset
uspto-grants-2009_05
Patent number
US07531570B2

Reaction notes

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