5-Fluoro-4-hydroxy-3-[1-(benzyloxycarbonyl)-2-piperidinecarboxamido]-pentanoic acid tert-butyl ester → 5-Fluoro-4-hydroxy-3-[2-piperidinecarboxamido]-pentanoic acid tert-butyl ester

HRID 1157139Notes

Reaction equation

HRID 1157139 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][CH:8]([NH:13][C:14]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][N:17]1C(OCC1C=CC=CC=1)=O)=[O:15])[CH:9]([OH:12])[CH2:10][F:11])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:32])[CH2:7][CH:8]([NH:13][C:14]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][NH:17]1)=[O:15])[CH:9]([OH:12])[CH2:10][F:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 694637995-Fluoro-4-hydroxy-3-[1-(benzyloxycarbonyl)-2-piperidinecarboxamido]-pentanoic acid tert-butyl ester

Product 1

HCID 694642585-Fluoro-4-hydroxy-3-[2-piperidinecarboxamido]-pentanoic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of [3S/R,4S/R,(2S)]-5-fluoro-4-hydroxy-3-[1-(benzyloxycarbonyl)-2-piperidinecarboxamido]-pentanoic acid tert-butyl ester (7.37 g, 16.29 mmol) in ethyl acetate (150 ml) was treated with 10% Pd/C (830 mg). The reaction mixture was then thoroughly degassed and placed under a hydrogen balloon. The resulting mixture was stirred at room temperature for 3 hrs after which it was filtered through celite and concentrated to the sub-title compound as a colorless gum (5.17 g, 100%): 1H NMR (400 MHz, CDCl3) δ 1.16-2.00 (15H, m), 2.51-2.78 (3H, m), 2.99-3.09 (1H, m), 3.18-3.28 (1H, m), 3.93-4.56 (4H, m), 7.39-7.58 (1H, m); 19F (376 MHz, CDCl3) δ −229.34 (t), −229.42 (t), −229.87 (t), 230.02 (t).

Workup

  1. customThe reaction mixture was then thoroughly degassed
  2. filtrationwas filtered through celite
  3. concentrationconcentrated to the sub-title compound as a colorless gum (5.17 g, 100%)

Sources & evidence

ORD record
ord-36cfa76053704827bf5b0957edeb020d
Source dataset
uspto-grants-2010_10
Patent number
US07807659B2

Reaction notes

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