Tetrahydrofuran → HCID 68869448, compound

HRID 1984820Notes

Reaction equation

[H-].[Na+].[C:3]([O:7][C:8](=[O:28])[NH:9][CH:10]([CH2:26][OH:27])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([Cl:25])[CH:19]=2)=[CH:14][CH:13]=1)([CH3:6])([CH3:5])[CH3:4].[CH2:29]1COCC1>CCOC(C)=O>[C:3]([O:7][C:8](=[O:28])[NH:9][CH:10]([CH2:26][O:27][CH3:29])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([Cl:25])[CH:19]=2)=[CH:14][CH:13]=1)([CH3:5])([CH3:4])[CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

NaH (55 mg, 1.31 mmol, 60% by wt suspension in mineral oil) was added at 0° C. to a solution of [2-(3′-Chloro-4′-fluoro-biphenyl-4-yl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester (0.5 g, 1.31 mmol) in 5 mL anhydrous THF and stirred for 20 min at 0° C. Mel (0.37 g, 2.63 mmol) was added to the reaction mixture and stirred for 6 h at room temperature. The reaction mixture was diluted with 5 mL EtOAc, and washed with water, brine and dried over Na2SO4. Solvent was removed under vacuum and silica gel chromatography (EtOAc: Hexanes) gave (R)-[[2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-methoxymethyl-ethyl]-carbamic acid tert-butyl ester (0.38 g). The Boc protecting group was removed by stirring the compound in 4M HCl in dioxane (5 ml) for 30 min. Evaporation of the solvent under vacuo gave (R)-2-(3′-chloro4′-fluoro-biphenyl-4-yl)-1-methoxymethyl-ethylamine hydrochloride.

Workup

additionMel (0.37 g, 2.63 mmol) was added to the reaction mixture
stirringstirred for 6 h at room temperature
washwashed with water, brine
dry with materialdried over Na2SO4
customSolvent was removed under vacuum and silica gel chromatography (EtOAc: Hexanes)

Sources & evidence

ORD record: ord-c5936a5cd740496ba7d4de57ebf09d6d
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544699B2

Reaction notes

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