Formaldehyde → HCID 66936334, compound

HRID 1366647Notes

Reaction equation

HRID 1366647 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C=O.[C:18](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:18][N:6]1[CH2:7][C@@H:2]([CH3:1])[N:3]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][C@H:5]1[CH3:8]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23402465324750-43-8

Product 1

HCID 66936334HCID 66936334, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2R,5R)-2,5-dimethyl-1-(phenylmethyl)piperazine (prepared according to J. Med. Chem. 2006, 49, 716-726, utilizing N-Boc-D-alanine in place of N-Boc-L-alanine) (667 mg, 3.26 mmol) in dichloromethane (25 mL) at 0° C. was added formaldehyde (0.367 mL, 37% water solution, 4.89 mmol) followed by sodium triacetoxyborohydride (900 mg, 4.24 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)-1,2,5-trimethyl-4-(phenylmethyl)piperazine (680 mg, 96%). LCMS: (M+H)+: 219.1.

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-a12d8b3b0ae44275a29a6bd71ae59287
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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