Sodium Hydroxide → (R)-N-[1-(3,4-Dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(pyridin-3-yl)-ethylamine

HRID 861442Notes

Reaction equation

HRID 861442 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH:19][CH2:20][C@H:21]([OH:29])[C:22]2[CH:23]=[CH:24][C:25](Cl)=[N:26][CH:27]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+].OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>C(O)C.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH:19][CH2:20][C@H:21]([OH:29])[C:22]2[CH:27]=[N:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 441036D-PsicoseHCID 86752026(R)-N-[1-(3,4-Dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine

Product 1

HCID 22881912(R)-N-[1-(3,4-Dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(pyridin-3-yl)-ethylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of (R)-N-[1-(3,4-dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine (100 mg, 0.26 mmol) in ethanol (7 mL) with 5N sodium hydroxide (0.1 mL, 0.5 mmol) was degassed with argon prior to the addition of Ni(R) (100 mg). The mixture was hydrogenated at 40 Psi overnight and then the catalyst was filtered through Celite and washed with a small amount of ethanol. The filtrate was stripped and the product was purified by prep TLC on silica gel (eluent: 5% methanol in methylene chloride) to give the titled compound. 1H NMR (500 MHz, CDCl3)δ 8.47 (m, 2H), 7.58 (m, 1H), 7.01-7.32 (m, 6H), 6.79-6.84 (m, 3H), 4.53-4.67 (m, 1H), 3.89 and 3.88(s, 3H, OCH3), 3.86 (s, 3H, OCH3), 3.79-3.85 (m, 1H), 2.90-3.03 (m, 2H), 2.78 (m, 1H), 2.49-2.50 (m, 1H).

Workup

  1. filtrationthe catalyst was filtered through Celite
  2. washwashed with a small amount of ethanol
  3. customthe product was purified by prep TLC on silica gel (eluent: 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-4e3b2729f90247efa47fa1b311a7c2d6
Source dataset
uspto-grants-1998_02
Patent number
US05714506

Reaction notes

Loading…