HCID 58906458, compound → 853953-22-7

HRID 1294582Notes

Reaction equation

HRID 1294582 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:16][N:17](CC2C=CC=CC=2)[CH3:18])([O:14][CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([O:14][CH3:15])([CH2:16][NH:17][CH3:18])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 58906458HCID 58906458, compound

Product 1

HCID 58906435853953-22-7Yield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

Amine (36) (55 g, 158 mmol) was dissolved in ethyl acetate (500 ml). Pd—C (10%, wet, 5 g) was added and the mixture was stirred for 23 h under hydrogen atmosphere (1 bar). TLC analysis revealed incomplete conversion. Extra Pd—C (2.5 g) was added and the mixture was stirred under H2 (1 bar) for 110 h. NMR analysis revealed complete conversion. The mixture was filtrated over Celite, the Celite crop was washed with ethyl acetate and the filtrate was evaporated to dryness. The residue was purified by distillation (bulb to bulb, 0.04 mbar, 130° C.) giving 35 g of compound (37) (86%) as colorless oil.

Workup

  1. stirringthe mixture was stirred under H2 (1 bar) for 110 h
  2. filtrationThe mixture was filtrated over Celite
  3. washthe Celite crop was washed with ethyl acetate
  4. customthe filtrate was evaporated to dryness
  5. distillationThe residue was purified by distillation (bulb to bulb, 0.04 mbar, 130° C.)

Sources & evidence

ORD record
ord-d0b2ac0b9ca14da9a693a28c02d6dc1c
Source dataset
uspto-grants-2007_07
Patent number
US07241770B2

Reaction notes

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