Dimethylamine → HCID 69105637, compound

HRID 31359Notes

Reaction equation

HRID 31359 reaction equation
C1C=C[C:4]2N(O)N=N[C:5]=2[CH:6]=1.C1CCC(N=[C:18]=[N:19][CH:20]2CCCCC2)CC1.C(OC([N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][C@H:34]1[C:39]([OH:41])=[O:40])=O)(C)(C)C.[CH3:42]NC.C[CH2:46][O:47]CC>C(Cl)Cl>[CH3:18][N:19]([CH3:20])[C:46]([C@:34]1([C:39]([O:41][C:5]([CH3:4])([CH3:6])[CH3:42])=[O:40])[CH2:35][CH2:36][CH2:37][CH2:38][NH:33]1)=[O:47]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 3283Diethyl EtherHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acid

Product 1

HCID 69105637HCID 69105637, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.2 g of HOBT and then 9.45 g of DCC are added at RT to a solution of 10 g of (2S)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (commercial) in 130 ml of DCM, and the mixture is left stirring for 1 hour. The reaction mixture is cooled on an ice bath, dimethylamine gas is added by bubbling for two times 10 minutes and the mixture is then left stirring overnight at RT. An insoluble material is filtered off and the filtrate is concentrated under vacuum. The residue is chromatographed on silica gel, eluting with a gradient of a DCM/MeOH mixture of from (98/2; v/v) to (96/4; v/v). The product obtained is taken up in ether and the precipitate is spin-filtered off. 8.5 g of the expected product are obtained.

Workup

  1. waitthe mixture is left
  2. temperatureThe reaction mixture is cooled on an ice bath
  3. customby bubbling for two times 10 minutes
  4. waitthe mixture is then left
  5. stirringstirring overnight at RT
  6. filtrationAn insoluble material is filtered off
  7. concentrationthe filtrate is concentrated under vacuum
  8. customThe residue is chromatographed on silica gel
  9. washeluting with a gradient of a DCM/MeOH mixture of from (98/2; v/v) to (96/4; v/v)
  10. customThe product obtained
  11. filtrationthe precipitate is spin-filtered off

Sources & evidence

ORD record
ord-e5bd49c7e1eb45de8aeb3a94bba23039
Source dataset
uspto-grants-2008_09
Patent number
US07425566B2

Reaction notes

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