Water → 2-t-Butoxycarbonyl-3,4-dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine

HRID 2301082Notes

Reaction equation

Cl.[CH2:2]1[C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH2:5][CH2:4][NH:3]1.[C:15](=[O:18])([O-])[O-:16].[K+].[K+].O>C(Cl)(Cl)Cl.CO>[C:6]([O:16][C:15]([N:3]1[CH2:4][CH2:5][C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[S:8][C:7]=2[CH2:2]1)=[O:18])([CH3:10])([CH3:7])[CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A 2.00 g (8.86 mmol) portion of 3,4-dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine hydrochloride was dissolved in a mixed solvent of 70 ml chloroform and 10 ml methanol, and the solution was mixed with 3.67 g (26.58 mmol) of potassium carbonate and cooled to 0° C. This was mixed with 2.24 ml (9.75 mmol) of di-t-butyl bicarbonate and stirred overnight at room temperature. The reaction solution was poured into ice-cooled water and extracted with chloroform. The extract was washed with water and dried (Na2SO4), and then the solvent was removed by evaporation under a reduced pressure and the thus obtained oily material was purified by a silica gel column chromatography (250 cc; elution by ethyl acetate-hexane=1:6) to obtain 2.04 g of the title compound (80% in yield).

Workup

additionThe reaction solution was poured into ice-
extractionextracted with chloroform
washThe extract was washed with water
dry with materialdried (Na2SO4)
customthe solvent was removed by evaporation under a reduced pressure
customthe thus obtained oily material was purified by a silica gel column chromatography (250 cc; elution by ethyl acetate-hexane=1:6)

Sources & evidence

ORD record: ord-e77133e75d3f45ec98581c4873708d02
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498251B1

Reaction notes

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