Methanol → HCID 178511713, compound

HRID 1846799Notes

Reaction equation

HRID 1846799 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][C@H:14]3[CH2:19][CH2:18][C@H:17]([N:20](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)[CH2:16][CH2:15]3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.CO>C(O)C.[OH-].[Pd+2].[OH-]>[O:1]1[CH2:2][CH2:3][CH:4]([C:7]2[C:8]([O:13][C@H:14]3[CH2:19][CH2:18][C@H:17]([NH2:20])[CH2:16][CH2:15]3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 887MethanolHCID 178491066HCID 178491066, compound

Product 1

HCID 178511713HCID 178511713, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Palladium hydroxide (0.040 g, 0.057 mmol, 20 weight % on carbon) was added to a stirred mixture of trans-4-(3-(3,6-dihydro-2H-pyran-4-yl)pyrazin-2-yloxy)-N,N-bis(4-methoxybenzyl)cyclohexanamine (0.40 g, 0.77 mmol) in ethanol (4 mL). The reaction mixture was placed under a hydrogen atmosphere (balloon) and stirred at 50° C. for 18 h. Additional palladium hydroxide (0.040 g) and methanol (1 mL) were added, and the reaction mixture was stirred at 50° C. for an additional 5 h. The reaction mixture was filtered, and the filtrate was concentrated. The resulting crude product was purified via silica gel chromatography to give trans-4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)cyclohexanamine as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for an additional 5 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe resulting crude product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-2d48001ef63b486c8caa935414e024c7
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

Loading…