Boron tribromide → HCID 131727301, compound

HRID 1727848Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[Cl:36])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([C@@H:19]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31]C)[C:20]([O:22][CH3:23])=[O:21])[CH2:15][CH2:14]2)[CH2:8][CH2:7]1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[Cl:36])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([C@@H:19]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[OH:31])[C:20]([O:22][CH3:23])=[O:21])[CH2:15][CH2:14]2)[CH2:10][CH2:11]1

Participants

Conditions

Temperature: -78 °C

Procedure

(αS) Methyl 4-[[4-(3,4-dichlorophenoxy)-1-piperidinyl]methyl]-α-[(2-methoxyphenyl)methyl]-1-piperidineacetate (120 mg) in dichloromethane (6 mL) was cooled to −78 C under nitrogen, and a 1M solution of boron tribromide in dichloromethane (9 mL) was added dropwise to it. The mixture was then stirred at −78° C. for 30 minutes, and then at −5° C. for 30 minutes. The reaction mixture was then quenched carefully with methanol (20 mL), allowed to warm to room temperature and the volatiles removed in. vacuo. The residue was purified by reverse-phase HPLC using 75:25 to 5:95 0.1% aqueous ammonium acetate/acetonitrile over 6 minutes, symmetry column. This gave 67 mg of the title compound as an oil.

Workup

waitat −5° C. for 30 minutes
customThe reaction mixture was then quenched carefully with methanol (20 mL)
temperatureto warm to room temperature
customthe volatiles removed in
customThe residue was purified by reverse-phase
customover 6 minutes

Sources & evidence

ORD record: ord-fbbc41e562164496a742e33323c9324d
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495013B2

Reaction notes

Loading…