Hydrochloric Acid → (R)-2-Amino-2-(5-fluoropyridin-2-yl)ethanol hydrochloride

HRID 450372Notes

Reaction equation

HRID 450372 reaction equation
[Si]([O:8][CH2:9][C@H:10]([NH:18]S(C(C)(C)C)=O)[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=1)(C(C)(C)C)(C)C.[ClH:25]>CO>[ClH:25].[NH2:18][C@H:10]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=1)[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68479628(RS)-N-[(1R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-(5-fluoropyridin-2-yl)ethyl]-2-methylpropane-2-sulfinamide2×

Product 1

HCID 68482269(R)-2-Amino-2-(5-fluoropyridin-2-yl)ethanol hydrochlorideYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (RS)—N-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-(5-fluoropyridin-2-yl)ethyl]-2-methylpropane-2-sulfinamide (Intermediate 22, 1.13 g, 3.02 mmol) in MeOH (15 ml) was added hydrochloric acid (4 M in dioxane, 3.02 ml, 12.08 mol) at 0° C. and the mixture was stirred for 15 minutes and was concentrated. The mixture was triturated from hexanes to provide the title salt (575 mg). The product is highly hygroscopic. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.62 (s, 1H) 8.55 (s, 2H) 7.76-7.93 (m, 1H) 7.65 (dd, J=8.29, 4.52 Hz, 1H) 4.43 (d, J=4.52 Hz, 1H) 3.77 (s, 2H).

Workup

  1. concentrationwas concentrated
  2. customThe mixture was triturated from hexanes

Sources & evidence

ORD record
ord-9356412212ae47449074dc5f80a317c9
Source dataset
uspto-grants-2013_07
Patent number
US08486966B2

Reaction notes

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