Ammonium formate → HCID 57032383, compound

HRID 2271009Notes

Reaction equation

HRID 2271009 reaction equation
C([O:8][CH2:9][C@H:10]1[C@@H:15]([CH3:16])[N:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][CH2:12][N:11]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].O.CO>[C:24]([O:23][C:21]([N:11]1[CH2:12][CH2:13][N:14]([S:17]([CH3:20])(=[O:19])=[O:18])[C@H:15]([CH3:16])[C@@H:10]1[CH2:9][OH:8])=[O:22])([CH3:26])([CH3:27])[CH3:25]

Participants

6

Reactant 2

HCID 2723923Ammonium formate3×HCID 54208445HCID 54208445, compound

Product 1

HCID 57032383HCID 57032383, compoundYield 92.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent2×HCID 962WaterSolvent3×

Procedure

10% Palladium on activated carbon (1.5 g) was suspended in H2O (10 ml) and the suspension was added to a solution of (2R,3R)-2-benzyloxymethyl-1-tert-butoxycarbonyl-4-methanesulfonyl-3-methyl-piperazine (2.1 g) and ammonium formate (3.3 g) in MeOH (25 ml). The mixture was refluxed for 1.5 hours. Ammonium formate (3.4 g) in H2O (10 ml) and MeOH (10 ml) were added to the reaction mixture, and the mixture was refluxed for 1.5 hours. 10% Palladium on activated carbon (1.5 g) in H2O (10 ml) and ammonium formate (3.4 g) were added to the reaction mixture and the mixture was refluxed for 2.5 hours. The catalyst was removed by filtration through a celite pad and the pad was washed with MeOH. The combined filtrate and washings were concentrated in vacuo. The residue was partitioned between AcOEt and brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give 1.5 g of (2R,3R)-1-tert-butoxycarbonyl-2-hydroxymethyl-4-methane-sulfonyl-3-methylpiperazine as a solid.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. temperaturethe mixture was refluxed for 1.5 hours
  3. temperaturethe mixture was refluxed for 2.5 hours
  4. customThe catalyst was removed by filtration through a celite pad
  5. washthe pad was washed with MeOH
  6. concentrationThe combined filtrate and washings were concentrated in vacuo
  7. customThe residue was partitioned between AcOEt and brine
  8. dry with materialThe organic layer was dried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ccfdac70f9243fd8f98d4d94e373f35
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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