HCID 86707859, compound → HCID 68309689, compound

HRID 922421Notes

Reaction equation

HRID 922421 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([N:17]([CH:33]2[CH2:35][CH2:34]2)[C:18]([C@@H:20]2[O:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]2)=[O:19])[CH3:16])=[CH:11][C:10]=1[O:36][CH2:37][CH2:38][CH2:39][O:40][CH3:41])C1C=CC=CC=1>CO.[Pd]>[CH:33]1([N:17]([C@@H:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([O:36][CH2:37][CH2:38][CH2:39][O:40][CH3:41])[CH:11]=2)[CH3:16])[C:18]([C@@H:20]2[O:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:21]2)=[O:19])[CH2:34][CH2:35]1

Participants

4

Reactant 1

HCID 86707859HCID 86707859, compound

Product 1

HCID 68309689HCID 68309689, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (2R)-2-{[{1-[4-(benzyloxy)-3-(3-methoxypropoxy)phenyl]ethyl}(cyclopropyl)amino]carbonyl}morpholin-4-carboxylate (1.45 g) in methanol 912 mL) was added 10% palladium on carbon (200 mg), and the mixture was stirred under hydrogen for 2 hours. An insoluble was filtered, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1→1/2) to give tert-butyl (2R)-2-[(cyclopropyl{(1R)-1-[4-hydroxy-3-(3-methoxypropoxy)phenyl]ethyl}amino)carbonyl]morpholin-4-carboxylate [Ex(169-1)] (913 mg) as a colorless oil.

Workup

  1. filtrationAn insoluble was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1→1/2)

Sources & evidence

ORD record
ord-342e0f67fe0b40aaa520d1f54c331b3b
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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