Formaldehyde → tert-Butyl 3-(hydroxymethyl)-4-methylpiperazine-1-carboxylate

HRID 467522Notes

Reaction equation

HRID 467522 reaction equation
[C:1]([O-])(=O)C.[Na+].C=O.C([BH3-])#N.[Na+].[OH:12][CH2:13][CH:14]1[NH:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1.C([O-])(O)=O.[Na+]>CO>[OH:12][CH2:13][CH:14]1[N:19]([CH3:1])[CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 223865084-N-Boc-2-hydroxymethylpiperazine

Product 1

HCID 66648821tert-Butyl 3-(hydroxymethyl)-4-methylpiperazine-1-carboxylateYield 58.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.303 g of sodium acetate, 0.375 g of formaldehyde and 0.218 g of sodium cyanoborohydride are added to a solution of 0.5 g of tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate in 50 ml of MeOH and stirred for 1 hour at RT. A saturated solution of NaHCO3 is added, it is extracted with DCM, the organic phase is dried over Na2SO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, eluting with DCM/MeOH mixture. 0.31 g of the expected compound is obtained.

Workup

  1. extractionit is extracted with DCM
  2. dry with materialthe organic phase is dried over Na2SO4
  3. customthe solvent is evaporated under vacuum
  4. customThe residue is chromatographed on silica gel
  5. washeluting with DCM/MeOH mixture

Sources & evidence

ORD record
ord-0d9e1d54cbe3490ab8bc1cf059690ff6
Source dataset
uspto-grants-2014_01
Patent number
US08623862B2

Reaction notes

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