2,7-Naphthyridine-2(1H)-carboxylic acid, 3,4-dihydro-, 1,1-dimethylethyl ester → tert-Butyl octahydro-2,7-naphthyridine-2(1H)-carboxylate

HRID 712487Notes

Reaction equation

[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[N:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[CH2:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][NH:8][CH2:9]2)[CH2:4][CH2:3][N:2]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of tert-butyl 3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate (1.00 g, 4.27 mmol, 1 eq) and Pd(OH)2 (400 mg, 0.1 eq) in 150 mL of acetic acid was heated at 80° C. overnight under Hz, then cooled to room temperature, filtered and concentrated in vacuo. To this, 100 mL of water was added. The mixture was adjusted to pH 7-8 with NH3—H2O, extracted with CH2Cl2 (50 mL×3). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, and the residue was purified by a silica gel column chromatography (10:1 (v/v) EtOAc/MeOH) to give the title compound as pale yellow oil (700 mg, 69%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 241.1 (M+1).

Workup

temperaturecooled to room temperature
filtrationfiltered
concentrationconcentrated in vacuo
additionTo this, 100 mL of water was added
extractionextracted with CH2Cl2 (50 mL×3)
dry with materialThe organic layer was dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customthe residue was purified by a silica gel column chromatography (10:1 (v/v) EtOAc/MeOH)

Sources & evidence

ORD record: ord-c896595c42cb4deea2cf29d9d3acae93
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181277B2

Reaction notes

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