Hydrochloric Acid → (2S)-2-amino-2-(pyridin-3-yl)ethan-1-ol dihydrochloride

HRID 539071Notes

Reaction equation

HRID 539071 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:17][S@](C(C)(C)C)=O)[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)(C(C)(C)C)(C)C.[ClH:24]>CO>[ClH:24].[ClH:24].[NH2:17][C@@H:10]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67033332(S)-N-((S)-2-(tert-butyldimethylsilyloxy)-1-(pyridin-3-yl)ethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 67033291(2S)-2-amino-2-(pyridin-3-yl)ethan-1-ol dihydrochlorideYield 16.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)—N—((S)-2-(tert-butyldimethylsilyloxy)-1-(pyridin-3-yl)ethyl)-2-methylpropane-2-sulfinamide (0.2 g, 1.77 mmol) in MeOH (9 mL) was treated with 4N hydrogen chloride (2.21 mL, 8.85 mmol) at 0° C. The mixture was allowed to warm up to ambient temperature and stirred for 1 hour. The mixture was concentrated and the residue treated with aqueous saturated NaHCO3/EtOAc. The organic layer was dried (phase separator silicone treated filter paper), concentrated. The residue was purified on silica gel (2-10% 7N ammonia in MeOH in DCM) to provide (S)-2-amino-2-(pyridin-3-yl)ethanol dihydrochloride (0.060 g, 16% yield) as a beige solid.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue treated with aqueous saturated NaHCO3/EtOAc
  3. customThe organic layer was dried
  4. addition(phase separator silicone treated filter paper)
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (2-10% 7N ammonia in MeOH in DCM)

Sources & evidence

ORD record
ord-29601bd83af849b1a574b338d875452d
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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