Hydrochloric Acid → tert-Butyl (2S)-2-(aminomethyl)azetidine-1-carboxylate

HRID 1671679Notes

Reaction equation

HRID 1671679 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[C:12](=O)[NH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>C1COCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][NH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 25417766HCID 25417766, compound

Product 1

HCID 51557287tert-Butyl (2S)-2-(aminomethyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a cold (0° C.) solution of (2S)-carbamoyl-azetidine-1-carboxylic acid tert-butyl ester (8 g) in dry THF (200 mL) was added dropwise 1M BH3 solution in THF (160 mL). The reaction mixture was stirred at RT under nitrogen for 20 h and cooled to 0° C. Then was added carefully 1M HCl solution (200 mL) and brine and the mixture was extracted with EA (3×). The aqueous phase was basified with 2M NaOH solution (pH 10), extracted with EA (3×). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated to yield the title compound light yellow oil (1.9 g, 25%).

Workup

  1. temperaturecooled to 0° C
  2. extractionthe mixture was extracted with EA (3×)
  3. extractionextracted with EA (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-300e1ba6e0a64fbfb2736d3e5c62fd0b
Source dataset
uspto-grants-2011_08
Patent number
US07994336B2

Reaction notes

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