Methyl valinate hydrochloride → Methyl (2S)-2-(hept-6-en-1-ylamino)-3-methylbutanoate

HRID 1879246Notes

Reaction equation

HRID 1879246 reaction equation
Cl.[NH2:2][C@H:3]([C:7]([O:9][CH3:10])=[O:8])[CH:4]([CH3:6])[CH3:5].[BH3-]C#N.[Na+].[CH:15](=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21]>CO.[Cl-].[Cl-].[Zn+2]>[CH2:21]([NH:2][C@@H:3]([CH:4]([CH3:6])[CH3:5])[C:7]([O:9][CH3:10])=[O:8])[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 111190Methyl valinate hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 52833206-Heptenal

Product 1

HCID 86637105Methyl (2S)-2-(hept-6-en-1-ylamino)-3-methylbutanoateYield 98%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution (0.3M) of L-valine, methyl ester, hydrochloride in dry MeOH was added ZnCl2 (1.0 eq.), NaCNBH3 (1.2 eq.), hept-6-enal 66 (1.2 eq.), and the reaction mixture was stirred at RT overnight. Then the volatiles were evaporated at reduced pressure and the residue taken-up in CH2Cl2 and washed with a saturated aq. solution of NaHCO3. The organic layer was dried over Na2SO4 and evaporated at reduced pressure affording the title compound (98%) as yellow pale oil.

Workup

  1. customThen the volatiles were evaporated at reduced pressure
  2. washthe residue taken-up in CH2Cl2 and washed with a saturated aq. solution of NaHCO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-566e2e43e35a48388320a4b6297222dc
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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