8-(4-Tert-butoxycarbonyl-piperazin-1-yl)-6-chloro-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid benzyl ester → 4-(3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 388278Notes

Reaction equation

HRID 388278 reaction equation
C(OC([N:11]1[C:16]2[CH:17]=[C:18](Cl)[CH:19]=[C:20]([N:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]3)[C:15]=2[O:14][CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[C:30]([O:29][C:27]([N:24]1[CH2:25][CH2:26][N:21]([C:20]2[C:15]3[O:14][CH2:13][CH2:12][NH:11][C:16]=3[CH:17]=[CH:18][CH:19]=2)[CH2:22][CH2:23]1)=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

4

Reactant 1

HCID 207656828-(4-Tert-butoxycarbonyl-piperazin-1-yl)-6-chloro-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid benzyl ester

Product 1

HCID 207656864-(3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-piperazine-1-carboxylic acid tert-butyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 8-(4-tert-butoxycarbonyl-piperazin-1-yl)-6-chloro-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid benzyl ester (640 mg, 1.32 mmol) in ethanol (10 mL) was hydrogenated at 50 psi in the presence of palladium on carbon for 12 hours. The catalyst was removed by filtration, and the filtrate was concentrated to give 4-(3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-piperazine-1-carboxylic acid tert-butyl ester as a light yellow solid (350 mg, 84%). MS: MH+=320.

Workup

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

Sources & evidence

ORD record
ord-dd21eb9274b043f6a44a4c2c78278469
Source dataset
uspto-grants-2013_02
Patent number
US08377931B2

Reaction notes

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