HCID 59600157, compound → HCID 66841436, compound

HRID 1929016Notes

Reaction equation

HRID 1929016 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:7][CH2:8][CH2:9][N:10]2[C:15](=[O:16])[CH2:14][O:13][CH2:12][C:11]=12)=[O:5])[CH3:2]>C(O)(=O)C.C(Cl)Cl.[Pt](=O)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH:11]2[CH2:12][O:13][CH2:14][C:15](=[O:16])[N:10]2[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 59600157HCID 59600157, compound

Product 1

HCID 66841436HCID 66841436, compoundYield 117.9%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 65 (225 mg, 1.0 mmol) in 5 ml of acetic acid is hydrogenated over 225 mg of platinum dioxide at RT and normal pressure for 18 hours. Another 225 mg of platinum dioxide is added and hydrogenation continued for 24 hours. The black suspension is diluted with 10 ml of DCM and filtered through a pad of celite. The filtrate is evaporated to give 268 mg of a yellow oil which is purified by chromatography (Biotage 12Si, 1=7.5 cm, ethyl acetate/ethanol 9:1).

Workup

  1. waithydrogenation continued for 24 hours
  2. filtrationfiltered through a pad of celite
  3. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-6c7113c58c6444b4a8c8d626a2bdc4d1
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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