Formaldehyde → HCID 57639110, compound

HRID 1366524Notes

Reaction equation

HRID 1366524 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.C=O.[C:18](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:8][C@H:6]1[N:7]([CH3:18])[C@@H:2]([CH3:1])[CH2:3][N:4]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:5]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10822535tert-butyl (3R,5S)-3,5-dimethylpiperazine-1-carboxylate

Product 1

HCID 57639110HCID 57639110, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl (3R,5S)-3,5-dimethyl-1-piperazinecarboxylate (2.04 g, 9.5 mmol) in dichloromethane (25 mL) at 0° C. was added formaldehyde (1.075 mL, 37% water solution, 14.3 mmol) followed by sodium triacetoxyborohydride (2.628 g, 12.4 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 2 h before being diluted with dichloromethane and washed with 1N NaOH solution. The organics were then washed with brine, dried (MgSO4) and evaporated to yield 1,1-dimethylethyl (3R,5S)-3,4,5-trimethyl-1-piperazinecarboxylate (2.06 g, 95%). LCMS: (M+H)+: 229.2.

Workup

  1. washwashed with 1N NaOH solution
  2. washThe organics were then washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-5d82372eac1d478ea338cbc12c8ee9ff
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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