Carbon Dioxide → [Rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-fluoro-ethyl]-amine

HRID 855208Notes

Reaction equation

[C:1]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][NH:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:29])CC.C(=O)(O)[O-].[Na+].C(=O)=O>C(Cl)Cl>[C:1]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][NH:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[F:29])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

159 mg of [rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine (0.5 mmol, described in example S43) in 5 ml DCM was cooled to 2° C. and treated with 0.2 ml of DAST (1.5 mmol) for 2 min. After 2 h stirring at 0° C. followed by 1 h at rt, the reaction mixture was again cooled down to 0° C. and treated with 5 ml saturated aqueous sodium bicarbonate. The reaction mixture was stirred until CO2 evolution stopped, then the organic phase was separated, washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was Purified by silicagel chromatography (40 g silica gel; heptane/EtOAc 2:1) leading to 27 mg of a light yellow semi-solid (17%). M(ISP) 320.3 (M+H)+.

Workup

customwas cooled to 2° C.
waitfollowed by 1 h at rt
temperaturethe reaction mixture was again cooled down to 0° C.
customthe organic phase was separated
washwashed with brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was Purified by silicagel chromatography (40 g silica gel; heptane/EtOAc 2:1)

Sources & evidence

ORD record: ord-27a180282cf84049863479db9e48078d
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

Loading…