Acetic Acid → Ethyl 3-amino-2-methylbutanoate

HRID 1888118Notes

Reaction equation

HRID 1888118 reaction equation
[NH2:1]/[C:2](/[CH3:10])=[C:3](/[CH3:9])\[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(#N)C>[NH2:1][CH:2]([CH3:10])[CH:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 5049666Sodium triacetoxyborohydrideHCID 53642952(Z)-3-Amino-2-methyl-2-butenoic Acid Ethyl Ester

Product 1

HCID 10341339Ethyl 3-amino-2-methylbutanoateYield 94.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (Z)-ethyl 3-amino-2-methylbut-2-enoate (Org. Lett. 2003, 5(25) 4779-4782, 1.1 g, 7.68 mmol) in acetonitrile (15 mL) was added sodium triacetoxyborohydride (4.88 g, 23.05 mmol) in one lot at RT. After the addition of acetic acid (2.0 mL, 34.9 mmol) (pH of reaction mixture ˜6.0), the contents were stirred at RT for 2.5 h. The reaction mixture was concentrated and partitioned between dichloromethane (60 mL) and 20% NaOH (10 mL). The dichloromethane layer is dried over sodium sulfate and concentrated to yield the title compound (1.05 g, 7.23 mmol, 94% yield) as an oil, which was used as such for the subsequent step without further purification. MS found: (M+H)+=146.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between dichloromethane (60 mL) and 20% NaOH (10 mL)
  3. dry with materialThe dichloromethane layer is dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c2edb1ee3c8e48ef8868e6bcc5798f52
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

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