HCID 67981633, compound → HCID 67981628, compound

HRID 1520038Notes

Reaction equation

HRID 1520038 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[CH2:14][C@@H:13]3[CH2:15][C@H:10]2[CH2:11][O:12]3)=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O.[Pd]>[C@H:13]12[CH2:15][C@H:10]([N:9]([CH2:8][C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:17][CH:16]=3)[CH2:14]1)[CH2:11][O:12]2

Participants

4

Reactant 1

HCID 67981633HCID 67981633, compound

Product 1

HCID 67981628HCID 67981628, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (1S,4S)-5-(4-nitrobenzyl)-2-oxa-5-azabicyclo[2.2.1]heptane (943 mg; 4.03 mmol; 1.0 eq.) in EtOAc (10 mL) was hydrogenated under 10 bars H2 in presence of Pd/C (moistened, 10%, 43 mg, 0.40 mmol; 0.1 eq.) O/N. The crude was filtered through a celite pad, concentrated under reduced pressure and purified by flash chromatography on silica (DCM:MeOH:NH4OH, 96:3:1) to give the title compound as an yellow oil (80 mg, 10%). 1H NMR (300 MHz, DMSO-d6) δ 6.95 (d, J=8.4 Hz, 2H), 6.54-6.44 (m, 2H), 4.91 (s, 2H), 4.31 (s, 1H), 3.87 (d, J=7.4 Hz, 1H), 3.58-3.41 (m, 3H), 3.35 (d, J=8.1 Hz, 1H), 2.66 (dd, J=9.9, 1.7 Hz, 1H), 2.34 (d, J=10.0 Hz, 1H), 1.74 (dd, J=9.5, 2.1 Hz, 1H), 1.54 (d, J=9.5 Hz, 1H).

Workup

  1. filtrationThe crude was filtered through a celite pad
  2. concentrationconcentrated under reduced pressure
  3. custompurified by flash chromatography on silica (DCM:MeOH:NH4OH, 96:3:1)

Sources & evidence

ORD record
ord-67742891e6d44c8aab1603faa61fa9f9
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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