Hydrochloric Acid → HCID 59396438, compound

HRID 2383066Notes

Reaction equation

[CH3:1][O:2][CH2:3][C@H:4]1[C:13]2[C:8](=[C:9]([CH3:14])[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]1[S@@](C1C=CC(C)=CC=1)=O.Cl.O.C(=O)([O-])[O-].[Na+].[Na+]>CCO.C1COCC1>[CH3:1][O:2][CH2:3][C@H:4]1[C:13]2[C:8](=[C:9]([CH3:14])[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][NH:5]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixed solution of (1R)-1-(methoxymethyl)-5-methyl-2-[(R)-(4-methylphenyl)sulfinyl]-1,2,3,4-tetrahydroisoquinoline (2.47 g) in EtOH (45 mL) and THF (10 mL) was added concentrated hydrochloric acid (3.1 mL) under stirring at 0° C., followed by further stirring for 10 minutes. To the mixture was added saturated sodium carbonate water (50 mL), followed by extraction with EtOAc. The organic layer was washed with a 1 M aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:EtOH:aqueous ammonia) to obtain (1R)-1-(methoxymethyl)-5-methyl-1,2,3,4-tetrahydroisoquinoline (1.276 g).

Workup

stirringby further stirring for 10 minutes
extractionfollowed by extraction with EtOAc
washThe organic layer was washed with a 1 M aqueous sodium hydroxide solution
dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (chloroform:EtOH:aqueous ammonia)

Sources & evidence

ORD record: ord-669aeb84c9c14b319e6f5d91238acbe4
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263607B2

Reaction notes

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