Hydrochloric Acid → (S)-3-Amino-4-cyclopropyl-2-methyl-butan-2-ol

HRID 927558Notes

Reaction equation

HRID 927558 reaction equation
[CH:1]1([CH2:4][C@H:5]([NH:10]C(=O)OC(C)(C)C)[C:6]([OH:9])([CH3:8])[CH3:7])[CH2:3][CH2:2]1.Cl>C(OCC)(=O)C.O>[NH2:10][C@@H:5]([CH2:4][CH:1]1[CH2:3][CH2:2]1)[C:6]([CH3:8])([OH:9])[CH3:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71087921(S)-tert-butyl 1-cyclopropyl-3-hydroxy-3-methylbutan-2-ylcarbamate

Product 1

HCID 86674766(S)-3-Amino-4-cyclopropyl-2-methyl-butan-2-olYield 69.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-tert-butyl 1-cyclopropyl-3-hydroxy-3-methylbutan-2-ylcarbamate (0.8 g, 3 mmol) in ethyl acetate was saturated with hydrochloride (10 mL) and stirred for 1 h at room temperature. After diluting with water (20 mL), the layers were separated and the water phase was washed with ethyl acetate (20 mL). Then it was adjusted with 1 N NaOH to pH=8˜9 and extracted with methylene chloride (3×20 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated to give the title compound as yellow oil (0.3 g, 64%); MS (EI): m/e=144.2 [M+Na]+.

Workup

  1. customthe layers were separated
  2. washthe water phase was washed with ethyl acetate (20 mL)
  3. extractionextracted with methylene chloride (3×20 mL)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dab2e1afe0504521bd6eaf96a8edfa28
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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