HCID 57554670, compound → HCID 57554633, compound

HRID 1511881Notes

Reaction equation

HRID 1511881 reaction equation
[NH2:1][C@:2]1([CH2:30][OH:31])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22]CC4C=CC=CC=4)=[CH:18][CH:17]=3)=[CH:9][CH:8]=2)[CH2:3]1>C(O)C.[Pd]>[NH2:1][C@:2]1([CH2:30][OH:31])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)=[CH:9][CH:8]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 57554670HCID 57554670, compound

Product 1

HCID 57554633HCID 57554633, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ((1R,3R)-1-amino-3-(4-(4-(benzyloxy)phenethoxy)phenyl)cyclopentyl)methanol (250 mg, 0.599 mmol) in ethanol (10 mL) was added Pd/C 10% (20 mg, 0.188 mmol). The mixture was flushed with hydrogen and hydrogenate with a balloon for about 16 hours. The crude mixture was filtered, concentrated and the residue was triturated with ether. The solid was collected and dried under vacuum at 50° C. to give 4-(2-(4-((1R,3R)-3-amino-3-(hydroxymethyl)cyclopentyl)phenoxy)ethyl)phenol (169 mg, 86%) as a white solid.

Workup

  1. customThe mixture was flushed with hydrogen and hydrogenate with a balloon for about 16 hours
  2. filtrationThe crude mixture was filtered
  3. concentrationconcentrated
  4. customthe residue was triturated with ether
  5. customThe solid was collected
  6. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-02477fa09a71453196059ad5ab490bc7
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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