Formaldehyde → HCID 66935783, compound

HRID 1366687Notes

Reaction equation

HRID 1366687 reaction equation
[CH3:1][C@@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][NH:4][C:3]1=[O:9].[CH2:10]=O.[BH4-].[Na+]>CO.ClCCl>[CH3:1][C@@H:2]1[N:7]([CH3:10])[C@@H:6]([CH3:8])[CH2:5][NH:4][C:3]1=[O:9]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 66936026HCID 66936026, compound

Product 1

HCID 66935783HCID 66935783, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,5S)-3,5-dimethyl-2-piperazinone in methanol (12 mL) at room temperature was added formaldehyde (0.345 mL, 37% water solution, 4.6 mmol) followed by sodium borohydride (261 mg, 6.9 mmol). The reaction mixture was stirred for 2 h before being diluted with dichloromethane and washed with 1N NaOH solution. The aqueous layer was back extracted with CH2Cl2 three times, and the combined organic layers were washed with brine, dried (MgSO4) and evaporated to yield (3S,5S)-3,4,5-trimethyl-2-piperazinone (128 mg, 39%). LCMS: (M+H)+: 143.1.

Workup

  1. washwashed with 1N NaOH solution
  2. extractionThe aqueous layer was back extracted with CH2Cl2 three times
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-6b74377d641441b6bb43f2d4a3f62b73
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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