Hydrochloric Acid → Tert-butyl 3-(1-aminoethyl)azetidine-1-carboxylate

HRID 245981Notes

Reaction equation

HRID 245981 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH:12]([NH:14]S(C(C)(C)C)=O)[CH3:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.O1CCOCC1>CO>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH:12]([NH2:14])[CH3:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 712800093-[1-(2-Methyl-propane-2-sulfinylamino)-ethyl]-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 71279891Tert-butyl 3-(1-aminoethyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution 3-[1-(2-methyl-propane-2-sulfinylamino)-ethyl]-azetidine-1-carboxylic acid tert-butyl ester (crude from step 2, 264 mg, 0.87 mmol) in MeOH at 0° C. was added 4.0 M HCl in dioxane (0.28 mL, 1.13 mmol) dropwise. The reaction mixture was stirred at 0° C. for 1 h then quenched with saturated aqueous NaHCO3, diluted with water and extracted with CH2Cl2 (3×). The combined organics were dried over MgSO4 and concentrated to afford 3-(1-amino-ethyl)-azetidine-1-carboxylic acid tert-butyl ester as a thick colorless oil which was used without further purification.

Workup

  1. customthen quenched with saturated aqueous NaHCO3
  2. additiondiluted with water
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-01867517183743f58816e8f675ffcb92
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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