(R)-3-methoxymethylamino-1-phenyl-1-propanol → (1R)-3-(methylamino)-1-phenylpropan-1-ol

HRID 2070355Notes

Reaction equation

HRID 2070355 reaction equation
CO[CH2:3][NH:4][CH2:5][CH2:6][C@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8]>CO.[Ni]>[CH3:3][NH:4][CH2:5][CH2:6][C@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8]

Participants

4

Reactant 1

HCID 67992341(R)-3-methoxymethylamino-1-phenyl-1-propanol

Product 1

HCID 7020931(1R)-3-(methylamino)-1-phenylpropan-1-ol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

The oily product of (R)-3-methoxymethylamino-1-phenyl-1-propanol obtained in example 2 was dissolved in 100 mL of methanol again with 1.2 g of Raney-nickel in a glass autoclave. The resulting solution was hydrogenated at 50° C. for 12 hours. Upon completion of hydrogenation, the reaction mixture was filtered and the solvent was removed under reduced pressure to obtain an objective compound as an oily compound (39.0 g, 96.5% by HPLC assay, 99% ee). The crude product was further purified by re-crystallization in toluene and heptane with optical purity as high as 100% ee. 1H NMR (400 MHz, CDCl3) δ (ppm)=1.7-1.8 (m, 1H), 1.8-1.9 (m, 1H), 2.5 (s, 3H), 2.8-2.9 (m, 2H), 4.9 (dd, J=3, 8.6 Hz, 1H), 7.3-7.4 (m, 5H).

Workup

  1. filtrationUpon completion of hydrogenation, the reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. customto obtain an objective compound as an oily compound (39.0 g, 96.5% by HPLC assay, 99% ee)
  4. customThe crude product was further purified by re-crystallization in toluene

Sources & evidence

ORD record
ord-d4882abf94ec46ad9fe22cddb209c34d
Source dataset
uspto-grants-2012_10
Patent number
US08299305B2

Reaction notes

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