Methanol → HCID 68619645, compound

HRID 1159357Notes

Reaction equation

HRID 1159357 reaction equation
[CH2:1]([N:8]([CH2:10][C@@H:11]1[CH2:14][C@H:13]([OH:15])[CH2:12]1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].C[OH:19]>[Pd]>[CH2:1]([N:8]([CH3:9])[C:10]([CH:11]1[CH2:12][C:13](=[O:15])[CH2:14]1)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 178418361HCID 178418361, compoundHCID 178482718HCID 178482718, compound

Product 1

HCID 68619645HCID 68619645, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

5% Pd/C (1 g) was added to a solution of intermediate 3, cis-3-{[Benzyl(methyl)amino]methyl}cyclobutanol (8.6 g, 0.042 mol) in MeOH (100 mL). The mixture was stirred in a flow of hydrogen for 48 h and filtered through Celite. The solid was washed on the filter with MeOH (2×50 mL). The filtrate was evaporated. Obtained crude intermediate 4 (5.3 g, ˜100%) was used in the next stage without additional purification. 1H NMR-data (DMSO-d6): 4.87-5.49 (br.s, 2H, NH, OH); 3.86-3.96 (m, 1H); 2.73 (d, 2H, CH2, J=7.1); 2.39 (s, 3H, NCH3); 2.24-2.34 (m, 2H); 1.85-1.97 (m, 1H); 1.46-1.57 (m, 2H).

Workup

  1. filtrationfiltered through Celite
  2. washThe solid was washed on the
  3. filtrationfilter with MeOH (2×50 mL)
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-ee92c4af665a418d9eb550f74112160c
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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