HCID 57425834, compound → HCID 66739287, compound

HRID 1727308Notes

Reaction equation

HRID 1727308 reaction equation
C([NH:8][CH:9]1[CH2:12][CH:11]([CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]1[F:22])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH2:15]([O:14][CH2:13][CH:11]1[CH2:12][CH:9]([NH2:8])[CH:10]1[F:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 57425834HCID 57425834, compound

Product 1

HCID 66739287HCID 66739287, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Benzyl-(3-benzyloxymethyl-2-fluoro-cyclobutyl)-amine (0.34 g, 1.21 mmol) was dissolved in 10 mL MeOH and this was treated with 20% Pd(OH)2 on carbon (0.07 g, 0.11 mmol). This was subjected to the hydrogenolysis conditions (50 psi). After 22 hr, the reaction mixture was filtered through celite and the filtrated was concentrated and was purified by silica gel flash chromatography (Hexane: EtOAc=1:1) to give 0.16 g (63%, Rf=0.30 (CH2Cl2:MeOH=15:1)). 1H NMR (CDCl3, 400 MHz): δ 2.08-2.16 (m, 2H), 2.96-3.12 (m, 1H), 3.52-3.64 (m, 2H), 3.88-3.94 (m, 1H), 4.55 (s, 2H), 5.03-5.19 (td, 1H, J=52.8, 6.0), 7.25-7.38 (m, 5H). 13C NMR (CDCl3, 100 MHz): δ 23.12-23.21 (d, J=9.0), 42.13-42.34 (d, J=21), 48.30, 70.07, 74.39, 87.46-89.63 (d, J=217), 128.98, 129.05, 129.61, 139.63. MS (FAB): expected for C12H16FNO (M+H)+ 210.26. Found 210.12885.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationthe filtrated was concentrated
  3. customwas purified by silica gel flash chromatography (Hexane: EtOAc=1:1)
  4. customto give 0.16 g (63%, Rf=0.30 (CH2Cl2:MeOH=15:1))

Sources & evidence

ORD record
ord-728471ce71114201b404f982485951bf
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

Loading…