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

HRID 1047597Notes

Reaction equation

HRID 1047597 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:10]1[O:14][N:13]=[C:12]([CH3:15])[N:11]=1)[CH3:9])(C)(C)C.Cl>O1CCOCC1>[CH3:15][C:12]1[N:11]=[C:10]([C@H:8]([NH2:7])[CH3:9])[O:14][N:13]=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 490-4.83 (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-ecf0d4af030b4e15a6fab483224c764f
Source dataset
uspto-grants-2013_10
Patent number
US08569512B2

Reaction notes

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