Hydrochloric Acid → HCID 59539668, compound

HRID 1842557Notes

Reaction equation

HRID 1842557 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:9]([NH:11]C(=O)OC(C)(C)C)[CH3:10])=[N+:6]([O-:8])[CH:7]=1.Cl.O1CCOCC1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:9]([NH2:11])[CH3:10])=[N+:6]([O-:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86657026HCID 86657026, compound

Product 1

HCID 59539668HCID 59539668, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [(1R)-1-(5-fluoro-1-oxidopyridin-2-yl)ethyl]carbamate (1.47 g, 5.74 mmol) in dichloromethane (28.7 mL) was added 4 M hydrochloric acid in 1,4-dioxane (43.0 mL, 172 mmol). After 2 h, concentration gave the title compound as a hydrochloride salt (1.396 g). MS 157.1 (M+1). 1H NMR (500 MHz, CD3OD): δ 8.55 (dd, J=4.3, 2.4 Hz, 1 H); 7.70 (dd, J=9.0, 6.7 Hz, 1 H); 7.52 (ddd, J=9.1, 7.1, 2.4 Hz, 1 H); 4.80 (q, J=7.0 Hz, 1 H); 1.74 (d, J=7.0 Hz, 3 H).

Workup

  1. concentrationconcentration

Sources & evidence

ORD record
ord-3d4f242240d1433e908e049c0ddf8ac2
Source dataset
uspto-grants-2015_02
Patent number
US08946231B2

Reaction notes

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