Hydrochloric Acid → HCID 90402207, compound

HRID 1854737Notes

Reaction equation

HRID 1854737 reaction equation
[ClH:1].[CH:2]1([C:5]([NH:12][S@@](C(C)(C)C)=O)([C:7]2[N:11]=[CH:10][O:9][N:8]=2)[CH3:6])[CH2:4][CH2:3]1>CO>[ClH:1].[CH:2]1([C:5]([C:7]2[N:11]=[CH:10][O:9][N:8]=2)([NH2:12])[CH3:6])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90402410HCID 90402410, compound

Product 1

HCID 90402207HCID 90402207, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HCl (1 ml, 2 mmol) (2.0 M in Et2O) was added to a stirring solution of (R)—N-(1-cyclopropyl-1-(1,2,4-oxadiazol-3-yl)ethyl)-2-methylpropane-2-sulfinamide (120 mg, 0.466 mmol) in MeOH (1 ml) at rt. The reaction was allowed to stir for 1 h at rt. The reaction was then concentrated to dryness azeotroping with toluene 3× to give the expected product 1-cyclopropyl-1-(1,2,4-oxadiazol-3-yl)ethanamine hydrochloride (87 mg, 0.46 mmol, 98% yield) consistent by NMR as a white solid. 1H NMR (500 MHz, METHANOL-d4) δ 9.38 (s, 1H), 1.67 (s, 3H), 1.44 (s, 1H), 0.74-0.66 (m, 2H), 0.62-0.56 (m, 1H), 0.51-0.45 (m, 1H).

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. customazeotroping with toluene 3×

Sources & evidence

ORD record
ord-c4dbe4349f554e2cb0e93e490523a1fa
Source dataset
uspto-grants-2015_02
Patent number
US08962651B2

Reaction notes

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