Formaldehyde → HCID 66935901, compound

HRID 1366538Notes

Reaction equation

HRID 1366538 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][C@H:5]([CH3:8])[CH2:4][N:3]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C=O.[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:1][C@H:2]1[CH2:7][N:6]([CH3:21])[C@H:5]([CH3:8])[CH2:4][N:3]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66936517HCID 66936517, compound

Product 1

HCID 66935901HCID 66935901, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of phenylmethyl trans-2,5-dimethyl-1-piperazinecarboxylate (enantiomeric mixture) (1.35 g, 5.43 mmol) in dichloromethane (40 mL) at 0° C. was added formaldehyde (0.817 mL, 37% water solution, 10.87 mmol) followed by sodium triacetoxyborohydride (1.726 g, 8.14 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 phenylmethyl trans-2,4,5-trimethyl-1-piperazinecarboxylate (enantiomeric mixture) (1.42 g, 100%). Phenylmethyl trans-2,4,5-trimethyl-1-piperazinecarboxylate (enantiomer 1) (480 mg) and phenylmethyl trans-2,4,5-trimethyl-1-piperazinecarboxylate (enantiomer 2) (400 mg) were separated by chiral chromatography. LCMS: (M+H)+: 263.3.

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-9d87ce1ac94943ccbade5a26e64a02d4
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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