Ammonium Chloride → HCID 57420366, compound

HRID 1842350Notes

Reaction equation

HRID 1842350 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-2e22cfb327974c32a5272f5b2e8591fe
Source dataset
uspto-grants-2015_02
Patent number
US08946217B2

Reaction notes

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