Methanol → HCID 86696737, compound

HRID 1774235Notes

Reaction equation

HRID 1774235 reaction equation
[CH:1]12[CH2:18][CH:4]([CH:5]([NH:7]C(=O)OCC3C=CC=CC=3)[CH2:6]1)[CH2:3][O:2]2.C[OH:20]>[Pd]>[NH2:7][CH:5]1[CH2:6][CH:1]2[CH2:18][CH:4]1[C:3](=[O:20])[O:2]2

Participants

4

Reactant 2

HCID 887MethanolHCID 86696716HCID 86696716, compound

Product 1

HCID 86696737HCID 86696737, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of benzyl 2-oxa-bicyclo[2.2.1]heptan-5-ylcarbamate (0.05 g, 2.0 mmol) and Pd/C (10%, 50 mg) in methanol (20 mL) was stirred under hydrogen atmosphere (1 atm) at room temperature for 16 hours. After completion of the reaction, the mixture was filtered through Celite®. The filtrate was concentrated under reduced pressure to afford 5-amino-2-oxa-bicyclo[2.2.1]heptan-3-one (360 mg, over 100%), which was used in the next step without further purification. LCMS (ESI) m/z: 128.1 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtered through Celite®
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3a7a00ccd01340ba90abfb698fecca9b
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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