P-Hydroxynorephedrine → Ritobegron ethyl

HRID 749623Notes

Reaction equation

C(O[CH:4](O)[CH2:5][C:6]1[C:18]([CH3:19])=[CH:17][C:9]([O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:8]([CH3:20])[CH:7]=1)C.[NH2:22][C@@H:23]([CH3:33])[C@@H:24]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[OH:25]>[C].[Pd].O1CCCC1>[OH:25][C@H:24]([C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1)[C@@H:23]([NH:22][CH2:4][CH2:5][C:6]1[C:18]([CH3:19])=[CH:17][C:9]([O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:8]([CH3:20])[CH:7]=1)[CH3:33]

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of ethyl 2-[4-(2-ethoxy-2-hydroxyethyl)-2,5-dimethylphenoxy]acetate (5.4 g), 10% palladium carbon (50% wet, 1.4 g), (1R,2S)-2-amino-1-(4-hydroxyphenyl)propan-1-ol (3.0 g) and tetrahydrofuran (30 g) was stirred under a hydrogen atmosphere at 40° C. for 3 hours. After the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was dissolved in toluene, and washed with water, an aqueous solution of sodium bicarbonate and brine successively. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give ethyl (−)-2-[4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methyethyl]amino]ethyl]-2,5-dimethylphenoxy]acetate (7.3 g).

Workup

customAfter the catalyst was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure
dissolutionThe residue was dissolved in toluene
washwashed with water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-ce881638664a4c38b3d56927b4f4835a
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402692B2

Reaction notes

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