Formaldehyde → HCID 11850017, compound

HRID 1978092Notes

Reaction equation

HRID 1978092 reaction equation
N1CCCCC1.C=O.[CH3:9][CH:10]([CH3:27])[CH2:11][C@@H:12]([C:24]([OH:26])=[O:25])[CH:13]([C:21](O)=O)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>C(O)(C)C>[C:17]([O:16][C:14]([C:13]([C@@H:12]([CH2:11][CH:10]([CH3:27])[CH3:9])[C:24]([OH:26])=[O:25])=[CH2:21])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 53789650HCID 53789650, compound

Product 1

HCID 11850017HCID 11850017, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

7.8 ml of piperidine and 20 ml of a 40% aqueous formaldehyde solution were added to a solution of 6.0 g of 1-tert.butyl dihydrogen 4-methyl-1(RS),1,2(R)-pentanetricarboxylate in 80 ml of isopropyl alcohol and the mixture was stirred overnight under a nitrogen atmosphere. The solvent was evaporated and the residue was dissolved in ethyl acetate. The ethyl acetate phase was washed in succession with 1M aqueous hydrochloric acid, warm water and brine and the dried over anhydrous magnesium sulphate. The solvent was evaporated to give 3.94 g of 2(R)-[1-(tertbutoxycarbonyl)vinyl]-4-methylvaleric acid in the form of a clear oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe ethyl acetate phase was washed in succession with 1M aqueous hydrochloric acid
  4. temperaturewarm water and brine
  5. dry with materialthe dried over anhydrous magnesium sulphate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-fb91918fda494ece9b56daf94b997f54
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

Loading…