Hydrochloric Acid → HCID 81899535, compound

HRID 1908667Notes

Reaction equation

HRID 1908667 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[CH:9][C:8]([C@@H:11]([NH:13][S@@](C(C)(C)C)=O)[CH3:12])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Cl>CO.O>[CH:1]([O:4][C:5]1[N:10]=[CH:9][C:8]([C@@H:11]([NH2:13])[CH3:12])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86675612HCID 86675612, compound

Product 1

HCID 81899535HCID 81899535, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

(R)-2-Methyl-propane-2-sulfinic acid [(S)-1-(6-isopropoxy-pyridin-3-yl)ethyl]-amide (2.90 g, 10.2 mmol) was dissolved in methanol (48 mL). A mixture of 12.0 M HCl in water (4.25 mL) and water (4.25 mL) was added drop wise over 3 minutes. The mixture was stirred at room temperature overnight. The mixture was evaporated to dryness. The oily residue was subjected to flash chromatography (silica, EtOAc/EtOH/triethylamine 90:5:5) on a short column to give (S)-1-(6-isopropoxy-pyridin-3-yl)-ethylamine IM24 (1.71 g, 93%) as a pale-yellow oil sufficiently pure for the next step. The overall yield from 1-(6-isopropoxy-pyridin-3-yl)-ethanone IM16 was 54%.

Workup

  1. additionwas added drop wise over 3 minutes
  2. customThe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-ec43d836ed0c4a2e8655149ec8457d8f
Source dataset
uspto-grants-2013_12
Patent number
US08598213B2

Reaction notes

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