tert-butyl 5-phenyl-2H-1,4-oxazine-4(3H)-carboxylate → Tert-butyl 3-phenylmorpholine-4-carboxylate

HRID 1615426Notes

Reaction equation

HRID 1615426 reaction equation
[C:1]1([C:7]2[N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:10][O:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([CH:7]2[CH2:12][O:11][CH2:10][CH2:9][N:8]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 86680663tert-butyl 5-phenyl-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 76620679Tert-butyl 3-phenylmorpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Tert-butyl 5-phenyl-2H-1,4-oxazine-4(3H)-carboxylate (170 mg, 0.65 mmol) was dissolved in methanol (10 ml). 10% Pd/c (100 mg) was added and the mixture stirred under hydrogen for 18 hours. The catalyst was removed by filtration and the filtrate concentrated to give crude tert-butyl 3-phenylmorpholine-4-carboxylate. The crude product was dissolved in DCM (10 ml) and TFA (1 ml) was added. The mixture was stirred at room temperature for 4 hours. The mixture was then concentrated and the crude purified by reverse phase HPLC (90/10 acetonitrile/water). The subtitle compound was obtained as a white solid (130 mg, 73%); 1H-NMR (d6-DMSO) 3.26 (2H, brm), 3.72-3.81 (2H, m), 4.00-4.03 (2H, m), 4.49 (1H, m), 7.45-7.53 (5H, m), 9.27 (2H, brs); 13C-NMR (d6-DMSO) 43.5, 57.7, 62.8, 68.2, 127.7, 128.9, 129.3; MS ES(+) 164.1 (M++1); HRMS m/z calcd for C10H13NO+H+ 164.1075 [M+H+]. Found 164.1082. IR λmax=1659 cm−1.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-b3fbb6b8791b455bba5be8ce77a645d1
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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