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

HRID 1615424Notes

Reaction equation

HRID 1615424 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:14][O:15][CH:16]=2)=[CH:7][CH:6]=1)=[O:4]>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[CH2:16][O:15][CH2:14][CH2:13][N:12]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 1

HCID 86680662tert-butyl 5-(4-(methoxycarbonyl)phenyl)-2H-1,4-oxazine-4(3H)-carboxylate

Product 1

HCID 86762486Tert-butyl 3-(4-(methoxycarbonyl)phenyl)morpholine-4-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a mixture of tert-butyl 5-(4-(methoxycarbonyl)phenyl)-2H-1,4-oxazine-4(3H)-carboxylate (50 mg, 0.156 mmol) in methanol (3 ml) was added Pd(OH)2/C (25 mg). The mixture was stirred under a hydrogen for 18 hrs. The mixture was filtered and concentrated to give the title compound as a yellow oil (47.6 mg, 95%). Data was identical to that described below.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-fdf126c1cd1a452189c69e1d80f6df3c
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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