trans-4-benzylhexahydro-2H-furo[3,4-b][1,4]oxazine → HCID 57870201, compound

HRID 81168Notes

Reaction equation

HRID 81168 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]2[CH2:14][O:15][CH2:16][C@@H:9]12)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[O:11]1[CH2:12][CH2:13][NH:8][C@@H:9]2[CH2:16][O:15][CH2:14][C@@H:10]12

Participants

4

Reactant 1

HCID 86724522trans-4-benzylhexahydro-2H-furo[3,4-b][1,4]oxazine

Product 1

HCID 57870201HCID 57870201, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of trans-4-benzylhexahydro-2H-furo[3,4-b][1,4]oxazine (600 mg, 2.73 mmol) in MeOH (10 mL) at room temperature was added Pd(OH)2/C (250 mg). Hydrogen was purged through the reaction for 10 minutes and then the reaction was stirred at room temperature under 1 atm of hydrogen for 2 hours. Concentrated HCl (0.3 mL) was added, and the solution was stirred for 15 minutes. The reaction was filtered through celite, and the solvent was evaporated to afford (trans)-hexahydro-2H-furo[3,4-b][1,4]oxazine (HCl salt, racemic). 1H NMR (400 MHz, CD3OD) δ 3.72-4.29 (m, 6H), 3.41-3.69 (m, 3H), 3.23-3.35 (m, 1H).

Workup

  1. customHydrogen was purged through the reaction for 10 minutes
  2. additionConcentrated HCl (0.3 mL) was added
  3. stirringthe solution was stirred for 15 minutes
  4. filtrationThe reaction was filtered through celite
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cbc0b74fc6ef484085f308ea867015f5
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

Loading…