(1R,3S)-methyl 1-amino-3-(4-(7-methoxyhept-1-ynyl)phenyl)cyclopentanecarboxylate → (1R,3S)-methyl 1-amino-3-(4-(7-methoxyheptyl)phenyl)cyclopentanecarboxylate

HRID 1511848Notes

Reaction equation

HRID 1511848 reaction equation
[NH2:1][C@:2]1([C:22]([O:24][CH3:25])=[O:23])[CH2:6][CH2:5][C@H:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:9][CH:8]=2)[CH2:3]1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:1][C@:2]1([C:22]([O:24][CH3:25])=[O:23])[CH2:6][CH2:5][C@H:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:9][CH:8]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 68936341(1R,3S)-methyl 1-amino-3-(4-(7-methoxyhept-1-ynyl)phenyl)cyclopentanecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 57554607(1R,3S)-methyl 1-amino-3-(4-(7-methoxyheptyl)phenyl)cyclopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(1R,3S)-methyl 1-amino-3-(4-(7-methoxyhept-1-ynyl)phenyl)cyclopentanecarboxylate was taken up in ethanol (14.94 ml). To this was added Pearlman's Catalyst (0.052 g, 0.075 mmol) and the mixture was stirred at ambient temperature under the atmosphere of hydrogen. After about 15 hours, the reaction mixture was filtered through Celite® and the filtrate was concentrated in vacuo to yield (1R,3S)-methyl 1-amino-3-(4-(7-methoxyheptyl)phenyl)cyclopentanecarboxylate (0.48 g, 1.38 mmol) as dark green oil.

Workup

  1. filtrationthe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-da48d54787224bdb882f0fd9c600dfe1
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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