(+/-)-6-(3-Methoxy-phenyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester → HCID 45074241, compound

HRID 60371Notes

Reaction equation

HRID 60371 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[CH:10]([O:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH:10]([OH:11])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 117720401(+/-)-6-(3-Methoxy-phenyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester

Product 1

HCID 45074241HCID 45074241, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (±)-6-(3-methoxy-phenyl)-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester (2 g) in methanol (115 mL) was added palladium on carbon 10% (10:90, palladium:carbon black, 400 mg). The mixture was shaken in a Parr apparatus under an atmosphere of hydrogen (50 PSI) overnight. Filtration through Celite and evaporation of the solvent provided the crude product. The product was purified by flash chromatography (Silicagel, EtOAc/hexanes) to give (±)-3-hydroxy-4-(3-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (1.79 g, 89% yield). 1H NMR (CDCl3): δ ppm 7.26 (s, 1H), 6.72-6.92 (m, 3H), 4.31 (br. s., 2H), 3.96 (br. s., 1H), 3.81 (s, 3H), 3.01 (d, J=13.4 Hz, 1H), 2.70-2.92 (m, 2H), 2.13-2.34 (m, 1H), 1.64 (br. s., 2H), 1.49 (s, 9H).

Workup

  1. filtrationFiltration
  2. customthrough Celite and evaporation of the solvent
  3. customprovided the crude product
  4. customThe product was purified by flash chromatography (Silicagel, EtOAc/hexanes)

Sources & evidence

ORD record
ord-92d129aa724f464f99804606cc90df33
Source dataset
uspto-grants-2016_09
Patent number
US09440984B2

Reaction notes

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