Ammonium Chloride → HCID 86645332, compound

HRID 1689923Notes

Reaction equation

HRID 1689923 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(C)(C)C)=[O:22])[CH2:12]1)=O.[Cl-].[NH4+]>C1COCC1>[OH:8][CH2:9][CH:11]1[N:16]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:15][CH2:14][N:13]([C:21]([OH:23])=[O:22])[CH2:12]1

Participants

5

Reactant 3

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

Product 1

HCID 86645332HCID 86645332, compound

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 tent-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-9bb8a0bf17b145ceb7e396fb0f77df20
Source dataset
uspto-grants-2012_04
Patent number
US08153629B2

Reaction notes

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