Boron tribromide → HCID 9841370, compound

HRID 1457534Notes

Reaction equation

[CH2:1]([S:3][C:4]1[O:5][C:6]2[C:14]([C@H:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][C@H:16]3[OH:22])=[C:13]([O:23]C)[CH:12]=[C:11]([O:25]C)[C:7]=2[C:8](=[O:10])[CH:9]=1)[CH3:2].B(Br)(Br)Br>ClCCCl>[CH2:1]([S:3][C:4]1[O:5][C:6]2[C:14]([C@H:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][C@H:16]3[OH:22])=[C:13]([OH:23])[CH:12]=[C:11]([OH:25])[C:7]=2[C:8](=[O:10])[CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of the title A compound (cis-(-)-2-(ethylthio)-8-(3-hydroxy-1-methyl-4-piperidinyl)-5,7-dimethoxy-4H-1-benzopyran-4-one: 180.5 mg, 0.476 mmol) in 1,2-dichloroethane (3 mL) was added a solution of BBr3 (2.5 mL of 2M solution in 1,2-dichloroethane). The mixture was stirred at 90° C. or 3 hours and cooled to room temperature. It was quenched by MeOH (5 mL) and concentrated. The residue was re-dissolved in MeOH (10 mL) and neutralized by aqueous NaHCO3 solution. The resulting solution was purified by HPLC (YMC OD S-10 30×500 mm; 45% B; flow rate 49 mL/minute; UV 254 nm). Those fractions containing the desired product were pooled, concentrated and lyophilized to afford the title compound (162 mg, 70%) as solid, mp 104° C. [α]D =-19.0° (MeOH, c 0.52).

Workup

temperaturecooled to room temperature
customIt was quenched by MeOH (5 mL)
concentrationconcentrated
dissolutionThe residue was re-dissolved in MeOH (10 mL)
customThe resulting solution was purified by HPLC (YMC OD S-10 30×500 mm; 45% B; flow rate 49 mL/minute; UV 254 nm)
additionThose fractions containing the desired product
concentrationconcentrated

Sources & evidence

ORD record: ord-12609a57fa214443864789dedd113088
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849733

Reaction notes

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