HCID 66798735, compound → HCID 66799292, compound

HRID 1193310Notes

Reaction equation

HRID 1193310 reaction equation
COC1C=CC(C[NH:8][CH:9]2[CH2:18][CH2:17][C:12]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:11][C:10]2([CH3:20])[CH3:19])=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:19][C:10]1([CH3:20])[CH:9]([NH2:8])[CH2:18][CH2:17][C:12]2([O:13][CH2:14][CH2:15][O:16]2)[CH2:11]1

Participants

4

Reactant 1

HCID 66798735HCID 66798735, compound

Product 1

HCID 66799292HCID 66799292, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

N-(4-Methoxybenzyl)-7,7-dimethyl-1,4-dioxaspiro[4.5]decan-8-amine (2.3 g, 7.54 mmol, 1 eq) was dissolved in MeOH (30 ml); Pd(OH)2 (690 mg) was added, and hydrogenation was carried out for 2 h at RT under balloon pressure (H2). After monitoring by thin-layer chromatography, the reaction mixture was filtered off over Celite and the filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography (Alox neutral, 1% methanol in dichloromethane). The desired product was obtained in the form of a yellow oil. Yield: 72% (1.0 g, 5.41 mmol).

Workup

  1. filtrationthe reaction mixture was filtered off over Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified by column chromatography (Alox neutral, 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b1bd5b9b359b47188e02827301b44ec6
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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