Hydrochloric Acid → HCID 131731314, compound

HRID 2364962Notes

Reaction equation

HRID 2364962 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][C@@H:12]([CH3:26])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[C:22]([F:25])([F:24])[F:23])(C(C)(C)C)(C)C.[ClH:27]>CO>[ClH:27].[F:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C@@H:12]([NH:11][CH2:10][CH2:9][OH:8])[CH3:26])=[C:16]([C:22]([F:23])([F:24])[F:25])[CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68380139HCID 68380139, compound

Product 1

HCID 131731314HCID 131731314, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Synthesis of 2-({(2S)-1-[(4-fluoro-2-(trifluoromethyl)phenoxy]propan-2-yl}amino)ethanol, hydrochloride salt (P4). To a solution of (2S)—N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1-[4-fluoro-2-(trifluoromethyl)phenoxy]propan-2-amine (C8) (460 mg, 1.16 mmol) in methanol (5 mL) was added a solution of hydrogen chloride (4N in dioxane, 2 mL). After 4 hours, the reaction mixture was concentrated in vacuo to afford the title compound as a clear gum. Yield: 398 mg, 100%. LCMS m/z 282.0 (M+1). 1H NMR (400 MHz, CD3OD) δ 1.51 (d, J=6.8 Hz, 3H), 3.28-3.32 (m, 2H, assumed; largely obscured by solvent peak), 3.80-3.87 (m, 1H), 3.84 (dd, J=5.3, 5.2 Hz, 2H), 4.29 (dd, half of ABX pattern, J=10.6, 5.8 Hz, 1H), 4.38 (dd, half of ABX pattern, J=10.6, 4.0 Hz, 1H), 7.30 (dd, J=9.0, 4.2 Hz, 1H), 7.38-7.45 (m, 2H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-13693b8a43c940e7aef67b249f22921e
Source dataset
uspto-grants-2014_04
Patent number
US08697673B2

Reaction notes

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