Formaldehyde → 4-((Tert-butoxy)carbonyl)-1-methylpiperazine-2-carboxylic acid

HRID 1661187Notes

Reaction equation

HRID 1661187 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:21](C)=O.[Na+].C([O-])(O)=O.[Na+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH3:21])[CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 51758554-[(Tert-butoxy)carbonyl]piperazine-2-carboxylic acid

Product 1

HCID 600810424-((Tert-butoxy)carbonyl)-1-methylpiperazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude piperazine-1,3-dicarboxylic acid-1-tert-butyl ester (4.92 mmol), prepared as described in 62(A), was suspended in dry acetonitrile (30 mL) under nitrogen atmosphere and formaldehyde (37% wt. aqueous solution, 367 mL, 4.92 mmol) and Na(OAc)3BH (2.3 g, 10.82 mmol) were added. The resulting mixture was stirred at R.T. for 3 h, then a saturated aqueous solution of NaHCO3 was slowly added until the pH was adjusted to 7. The mixture was concentrated to dryness under reduced pressure to give a yellow solid that was used without further purification for the next step.

Workup

  1. concentrationThe mixture was concentrated to dryness under reduced pressure
  2. customto give a yellow solid that
  3. customwas used without further purification for the next step

Sources & evidence

ORD record
ord-71de8e05e1904eb99b495e5995e6a7a8
Source dataset
uspto-grants-2011_10
Patent number
US08030331B2

Reaction notes

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