Hydrochloric Acid → (R)-1-(3-Methyl-1,2,4-oxadiazol-5-yl)ethan-1-amine

HRID 592271Notes

Reaction equation

HRID 592271 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C@H:7]([NH:9]C(=O)OC(C)(C)C)[CH3:8])[O:4][N:3]=1.Cl>O1CCOCC1>[CH3:1][C:2]1[N:6]=[C:5]([C@H:7]([NH2:9])[CH3:8])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86657025Tert-butyl (R)-(1-(3-methyl-1,2,4-oxadiazol-5-YL)ethyl)carbamate

Product 1

HCID 28948822(R)-1-(3-Methyl-1,2,4-oxadiazol-5-yl)ethan-1-amineYield 151.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl [(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]carbamate (6.0 g, 26.4 mmol) in dioxane (40 mL) was added 4 M hydrochloric acid in dioxane (30 mL). The reaction mixture was stirred for 16 h. The solution was concentrated and dried by vacuum to give hydrochloride salt of (1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine (5.1 g). 1H NMR (500 MHz, CD3OD): δ 4.90-4.83 (m, 1H); 2.41 (s, 3H); 1.72 (d, J=7.0 Hz, 3H). MS 128.2 (M+1).

Workup

  1. concentrationThe solution was concentrated
  2. customdried by vacuum

Sources & evidence

ORD record
ord-75464fa2093d433f815b987a42a47e6f
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

Loading…