HCID 178501082, compound → HCID 178501083, compound

HRID 352686Notes

Reaction equation

HRID 352686 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][CH2:22][N:21]3[CH3:25])=[CH:16][N:15]=2)[CH2:7][CH2:6]1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][CH2:22][N:21]3[CH3:25])=[CH:16][N:15]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 178501082HCID 178501082, compound

Product 1

HCID 178501083HCID 178501083, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5 (0.13 g, 0.4 mmol) in MeOH (40 mL) was hydrogenated at room temperature and atmospheric pressure over 10% Pd/C (0.06 g). After 40 min the catalyst was filtered off and washed with MeOH. The volatiles was evaporated under reduced pressure and the residue was chromatographed [SiO2, acetone/iso-hexane (1:2)] to afford 0.13 g (93%) of 6.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationAfter 40 min the catalyst was filtered off
  3. washwashed with MeOH
  4. customThe volatiles was evaporated under reduced pressure
  5. customthe residue was chromatographed [SiO2, acetone/iso-hexane (1:2)]

Sources & evidence

ORD record
ord-8b0d271e3bd24c5794cd90e65fb9260e
Source dataset
uspto-grants-2004_06
Patent number
US06747156B2

Reaction notes

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