HCID 67290358, compound → HCID 24739418, compound

HRID 603330Notes

Reaction equation

HRID 603330 reaction equation
C([NH:8][CH:9]([C:16]([O:21][CH3:22])([O:19][CH3:20])[CH2:17][F:18])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])C1C=CC=CC=1>CO.[Pd]>[NH2:8][CH:9]([C:16]([O:21][CH3:22])([O:19][CH3:20])[CH2:17][F:18])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 1

HCID 67290358HCID 67290358, compound

Product 1

HCID 24739418HCID 24739418, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl 3-(benzylamino)-5-fluoro-4,4-dimethoxypentanoate (7, R1=ethyl, R2=methyl, R4=benzyl, R5=hydrogen, 32.1 g, 103 mmol) in methanol (321 mL) was treated with 10% palladium catalyst (10% Pd/C) under hydrogen atmosphere (1 atm) for 4 h. The crude mixture was filtered through a pad of Celite® (96 g), washed with methanol (160 mL), and the filtrate was concentrated under reduced pressure to give the title compound (1, R1=ethyl, R2=methyl, 21.4 g, 94%), which was used in the next reaction.

Workup

  1. filtrationThe crude mixture was filtered through a pad of Celite® (96 g)
  2. washwashed with methanol (160 mL)
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-22b426a9440d4fb5946314113de7d093
Source dataset
uspto-grants-2011_03
Patent number
US07906676B2

Reaction notes

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