Formaldehyde → HCID 66936264, compound

HRID 1366567Notes

Reaction equation

HRID 1366567 reaction equation
[CH3:1][CH:2]([C@@H:4]1[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:7][NH:6][CH2:5]1)[CH3:3].[C:17](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>C(Cl)Cl>[CH3:17][N:6]1[CH2:7][CH2:8][N:9]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[C@@H:4]([CH:2]([CH3:1])[CH3:3])[CH2:5]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 17750439(2S)-2-Isopropylpiperazine, N1-BOC protected

Product 1

HCID 66936264HCID 66936264, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Commercially-available (S)—N-1-Boc-2-isopropylpiperazine (2.0 g, 8.76 mmol), sodium triacetoxyborohydride (2.76 g, 13 mmol), and formaldehyde (37% in H2O, 1.06 mL, 13 mmol) were dissolved and stirred in CH2Cl2 (40 mL) overnight at room temperature. After this time, the reaction mixture was diluted with additional CH2Cl2 and washed with 1 N NaOH and brine. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to provide 1,1-dimethylethyl (2S)-4-methyl-2-(1-methylethyl)-1-piperazinecarboxylate (2.18 g) as a colorless oil.

Workup

  1. washwashed with 1 N NaOH and brine
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c9996f2d1b943fa96c8e5f4ad04c254
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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