Piperidine → HCID 131713005, compound

HRID 851727Notes

Reaction equation

HRID 851727 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C(OCC)(=O)C>[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

Product 1

HCID 131713005HCID 131713005, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

3.46 g (15 mmoles) of BOC-Leu-OH are dissolved in 50 ml of ethyl acetate, 2.1 ml (15 mmoles) of triethylamine are added, and the solution is cooled to -15° C. The mixture is stirred at the same temperature, and 1.97 ml (16 mmoles) of pivaloyl chloride are added dropwise, followed by 1.65 ml (16.5 mmoles) of piperidine. The mixture is stirred for 10 minutes between the introduction of the two reactants. When the addition is complete, the mixture is stirred for additional 30 minutes at -10° C., and then it is allowed to stand in a refrigerator overnight. The separated precipitate is filtered off, the filtrate is washed thrice with 10 ml of n hydrochloric acid, each, thrice with 10 ml of n sodium hydrocarbonate solution, each, and then with 10 ml of water, dried over anhydrous sodium sulfate, and evaporated. The oily residue is dissolved in 15 ml of a 4 n solution of hydrochloric acid in ethyl acetate, the mixture is allowed to stand for one hour, then it is diluted with ether and stored in a refrigerator overnight. The precipitate is filtered off to obtain 2.0 g (57%, calculated for BOC-Leu-OH) of H-Leu-piperidine.HCl; m.p.: 123°-125° C., Rf5 =0.45.

Workup

  1. additionare added dropwise
  2. additionWhen the addition
  3. stirringthe mixture is stirred for additional 30 minutes at -10° C.
  4. customto stand in a refrigerator overnight
  5. filtrationThe separated precipitate is filtered off
  6. washthe filtrate is washed thrice with 10 ml of n hydrochloric acid
  7. dry with materialeach, thrice with 10 ml of n sodium hydrocarbonate solution, each, and then with 10 ml of water, dried over anhydrous sodium sulfate
  8. customevaporated
  9. dissolutionThe oily residue is dissolved in 15 ml of a 4 n solution of hydrochloric acid in ethyl acetate
  10. waitto stand for one hour
  11. additionit is diluted with ether
  12. customstored in a refrigerator overnight
  13. filtrationThe precipitate is filtered off

Sources & evidence

ORD record
ord-6083b7663340487cb153f824dd1bc2f3
Source dataset
uspto-grants-1983_05
Patent number
US04386073

Reaction notes

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