Ammonium Chloride → HCID 57420366, compound

HRID 2353166Notes

Reaction equation

HRID 2353166 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([CH:11]1[N:16]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:15][CH2:14][N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:12]1)=O.[Cl-].[NH4+]>C1COCC1>[C:24]([O:23][C:21]([N:13]1[CH2:14][CH2:15][N:16]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:11]([CH2:9][OH:8])[CH2:12]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 57494066HCID 57494066, compound

Product 1

HCID 57420366HCID 57420366, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminium hydride (0.75 g) in THF (30 mL) was added a solution of 4-methanesulfonyl-piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (3.2 g) in THF (20 mL) at 0° C. The reaction mixture was subsequently warmed to room temperature. After stirring for 2.5 h, ammonium chloride solution (5 mL) was added to the reaction mixture, which was then filtered through celite, washed with brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography to yield 3-hydroxymethyl-4-methanesulfonyl-piperazine-1-carboxylic acid tert-butyl ester (1.13 g). Treatment of this compound with HCl in DCM/MeOH yielded the desired amine, which was isolated as the hydrochloride salt.

Workup

  1. filtrationwas then filtered through celite
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-cca2531fe1464f16bddabcfec646ec4e
Source dataset
uspto-grants-2010_07
Patent number
US07750002B2

Reaction notes

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