Hydrochloric Acid → (1R)-1-(Pyridin-2-yl)ethan-1-amine--hydrogen chloride (1/2)

HRID 246008Notes

Reaction equation

HRID 246008 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]([NH:9][S@@](C(C)(C)C)=O)[CH3:8].[ClH:16].O1CCOCC1>CO>[ClH:16].[ClH:16].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]([NH2:9])[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71288321HCID 71288321, compound

Product 1

HCID 56973375(1R)-1-(Pyridin-2-yl)ethan-1-amine--hydrogen chloride (1/2)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-2-methyl-propane-2-sulfinic acid ((R)-1-pyridin-2-yl-ethyl)-amide (1.10 g, 4.86 mmol) in MeOH (12 mL) was added 4.0 M hydrogen chloride in dioxane (3.04 mL, 12.1 mmol). The reaction mixture was stirred at room temperature for 30 min then concentrated and dried under high vacuum to afford 1.0 g of (R)-1-pyridin-2-yl-ethylamine dihydrochloride as a light yellow solid. 1H NMR (METHANOL-d4, 300 MHz): δ (ppm) 8.80 (t, J=3.8 Hz, 1H), 8.32 (tdd, J=7.9, 4.5, 1.7 Hz, 1H), 7.88 (dd, J=7.9, 4.5 Hz, 1H), 7.72-7.83 (m, 1H), 4.78 (qd, J=6.9, 4.5 Hz, 1H), 1.73 (dd, J=6.9, 4.5 Hz, 3H). Assume 82% ee based on 10:1 dr of the starting material.

Workup

  1. concentrationthen concentrated
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-7e5cac9ff9ae4cce9294bb51ffeff61f
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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