Hydrochloric Acid → 2-(2-Azabicyclo[2.2.1]heptan-5-yloxy)ethanol

HRID 928565Notes

Reaction equation

HRID 928565 reaction equation
C(OC([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][CH:11]2[O:15][CH2:16][CH2:17][O:18]C1CCCCO1)=O)(C)(C)C.Cl.[OH-].[Na+]>C1COCC1>[CH:9]12[CH2:14][CH:12]([CH:11]([O:15][CH2:16][CH2:17][OH:18])[CH2:10]1)[CH2:13][NH:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89579665Tert-butyl-5-(2-tetrahydropyran-2-yloxyethoxy)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 895794962-(2-Azabicyclo[2.2.1]heptan-5-yloxy)ethanolYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl-5-(2-tetrahydropyran-2-yloxyethoxy)-2-azabicyclo[2.2.1]heptane-2-carboxylate (1.08 g, 3.16 mmol) was stirred overnight in 5 M hydrochloric acid (30 mL, 990 mmol)/THF (30 mL). The reaction mixture was basified with NaOH and washed with DCM. The organic was dried over Na2SO4 and concentrated in vacuo to afford 2-(2-azabicyclo[2.2.1]heptan-5-yloxy)ethanol (350 mg). LCMS RT=0.57 min. M+1=158.

Workup

  1. washwashed with DCM
  2. dry with materialThe organic was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66bf81bcaed541118c4789294fb2b8a2
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

Loading…