Hydrochloric Acid → 3-Pyrimidin-2-yl-8-azabicyclo[3.2.1]octan-3-ol hydrochloride

HRID 2373537Notes

Reaction equation

HRID 2373537 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1)([OH:16])[CH2:12]2)C1C=CC=CC=1.[ClH:23]>[Pd].C(O)C>[ClH:23].[N:18]1[CH:19]=[CH:20][CH:21]=[N:22][C:17]=1[C:11]1([OH:16])[CH2:12][CH:13]2[NH:8][CH:9]([CH2:15][CH2:14]2)[CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 692005418-Benzyl-3-pyrimidin-2-yl-8-azabicyclo[3.2.1]octan-3-ol

Product 1

HCID 674651293-Pyrimidin-2-yl-8-azabicyclo[3.2.1]octan-3-ol hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In an autoclave, 8-benzyl-3-pyrimidin-2-yl-8-azabicyclo[3.2.1]octan-3-ol (5.0 g, 17 mmol), palladium on charcoal (3,5 g, 5% Pd/C, 50% water wet) ethanol (27.5 ml) and 2N HCl (2.5 ml) were mixed and hydrogenated under a pressure of 0.5 to 1.5 bar at 50° C. The reaction was followed by HPLC. After complete reaction (6 to 8 h) the mixture was filtered and the residue washed with ethanol. The filtrate was concentrated to dryness under vacuum at 50° and the crude product is purified by column chromatography (90 g silica gel, methanol:ammonia (25%) 50:1). Yield: 1.8 g (52%) as free base. Assay (HPLC): 99% area.

Workup

  1. customAfter complete reaction (6 to 8 h) the mixture
  2. filtrationwas filtered
  3. washthe residue washed with ethanol
  4. concentrationThe filtrate was concentrated to dryness under vacuum at 50°
  5. customthe crude product is purified by column chromatography (90 g silica gel, methanol:ammonia (25%) 50:1)

Sources & evidence

ORD record
ord-8521b01d4540465fb455b1318ccd8401
Source dataset
uspto-grants-2008_12
Patent number
US07459556B2

Reaction notes

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