Formaldehyde → HCID 29920718, compound

HRID 1366445Notes

Reaction equation

HRID 1366445 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[CH2:15]=O>C(Cl)Cl>[CH3:1][C@@H:2]1[N:7]([CH3:15])[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 7023035(S)-1-Boc-3-methylpiperazine

Product 1

HCID 29920718HCID 29920718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercially available 1,1-dimethylethyl (3S)-3-methyl-1-piperazinecarboxylate (3.05 g, 15.23 mmol), formaldehyde (37% in water) (2.13 mL), sodium triacetoxy borohoydride (5.52 g, 26.04 mmol) and DCM (250 mL) were stirred overnight. The solvent was removed, and 1N NaOH was added to the residue. The mixture was extracted with dichloromethane, and the organics were dried (Na2SO4) and concentrated in vacuo to provide 1,1-dimethylethyl (3S)-3,4-dimethyl-1-piperazinecarboxylate as a clear oil (3.15 g. 97%). LCMS: (M+H)+=215.3.

Workup

  1. customThe solvent was removed
  2. addition1N NaOH was added to the residue
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialthe organics were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6355703e727f4b938542aedbc5f5c2d0
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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