HCID 67313842, compound → HCID 86761354, compound

HRID 1010904Notes

Reaction equation

HRID 1010904 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([C:19]2[CH:24]=[CH:23][C:22]([C@@H:25]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH3:26])=[CH:21][CH:20]=2)[OH:18])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>O1CCCC1.CC(O)C.[OH-].[Pd+2].[OH-]>[C:31]([O:30][C:28](=[O:29])[NH:27][C@H:25]([C:22]1[CH:23]=[CH:24][C:19]([CH:17]([OH:18])[CH:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)=[CH:20][CH:21]=1)[CH3:26])([CH3:32])([CH3:33])[CH3:34]

Participants

5

Reactant 1

HCID 67313842HCID 67313842, compound

Product 1

HCID 86761354HCID 86761354, compoundYield 108.1%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution prepared by dissolving 2.98 g of the compound [25-1] in a mixed solvent of 30 mL of tetrahydrofuran and 10 mL of 2-propanol, 750 mg of a carbon catalyst of 20% palladium hydroxide was added, and the mixture was stirred overnight at room temperature under hydrogen atmosphere. The catalyst was filtered through celite, and the filtrate was concentrated under reduced pressure, to obtain 2.3 g of tert-butyl((1S)-1-{4-[hydroxy(piperidin-4-yl)methyl]phenyl}ethyl)carbamate [33-3] (hereinafter, referred to as the compound [33-3]). The compound [33-3] was used in the subsequent reaction without further purification.

Workup

  1. customTo a solution prepared
  2. additionwas added
  3. filtrationThe catalyst was filtered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-34124980b9084b6e834ef17296fae27e
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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