HCID 57425834, compound → HCID 66739287, compound

HRID 1641497Notes

Reaction equation

HRID 1641497 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-1647650f591741dbbd9c47f65f6b4183
Source dataset
uspto-grants-2012_02
Patent number
US08114994B2

Reaction notes

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