Formaldehyde → HCID 66936524, compound

HRID 1366693Notes

Reaction equation

HRID 1366693 reaction equation
[CH2:1]([C@@H:3]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:6]([CH3:16])[CH2:5][NH:4]1)[CH3:2].C=O.[C:19](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:1]([C@@H:3]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:6]([CH3:16])[CH2:5][N:4]1[CH3:19])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66936270HCID 66936270, compound

Product 1

HCID 66936524HCID 66936524, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2R,5R)-5-ethyl-2-methyl-1-(phenylmethyl)piperazine (prepared according to procedures in J. Med. Chem. 2006, 49, 716-726, utilizing Boc-D-2-aminobutyric acid in place of N-Boc-L-alanine) (902 mg, 4.13 mmol) in dichloromethane (25 mL) at 0° C. was added formaldehyde (0.435 mL, 37% water solution, 5.78 mmol) followed by sodium triacetoxyborohydride (1050 mg, 4.96 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 washed with brine, dried (MgSO4) and evaporated to yield (2R,5R)-2-ethyl-1,5-dimethyl-4-(phenylmethyl)piperazine (875 mg, 91%). LCMS: (M+H)+: 233.3.

Workup

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

Sources & evidence

ORD record
ord-22d6aac2f98a4b2590cff261b9b61000
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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