HCID 67296390, compound → HCID 59617435, compound

HRID 2276836Notes

Reaction equation

HRID 2276836 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:19][CH2:18][C@H:17]([NH:20][C@@H:21]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][CH:24]=3)[CH3:22])[CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:23]1([C@H:21]([NH:20][C@H:17]2[CH2:18][CH2:19][C@@H:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[CH2:16]2)[CH3:22])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 67296390HCID 67296390, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59617435HCID 59617435, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a nitrogen stream, (1S,3R)-3-[4-(benzyloxy)phenyl]-N-[(1R)-1-(naphthalen-1-yl)ethyl]cyclopentanamine (740 mg, 1.8 mmol) was dissolved in methanol (10 mL). After adding 10% palladium/carbon (70 mg) to the mixture, the atmosphere was replaced with hydrogen, and then the mixture was stirred for 16 hours at room temperature. The catalyst was filtered off, and the solvent of the filtrate was distilled off under reduced pressure. The residue obtained was purified by column chromatography (methanol/methylene chloride: 0/100-10/90) to give the title compound (427 mg, 73%).

Workup

  1. filtrationThe catalyst was filtered off
  2. distillationthe solvent of the filtrate was distilled off under reduced pressure
  3. customThe residue obtained
  4. customwas purified by column chromatography (methanol/methylene chloride: 0/100-10/90)

Sources & evidence

ORD record
ord-fce4ab63ea964a8c86aca03e9a9eff19
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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