Water → HCID 6481587, compound

HRID 335007Notes

Reaction equation

HRID 335007 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]2[N:24]([CH2:25][C:26]3[C:31]([OH:32])=[CH:30][CH:29]=[C:28]([CH3:33])[N:27]=3)[C:23]3[CH:34]=[C:35]([CH3:39])[CH:36]=[C:37]([CH3:38])[C:22]=3[N:21]=2)[CH2:15][CH2:14]1)C.O.C(OC(=O)C)C>O1CCCC1>[OH:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]2[N:24]([CH2:25][C:26]3[C:31]([OH:32])=[CH:30][CH:29]=[C:28]([CH3:33])[N:27]=3)[C:23]3[CH:34]=[C:35]([CH3:39])[CH:36]=[C:37]([CH3:38])[C:22]=3[N:21]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 6481592HCID 6481592, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 6481587HCID 6481587, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

LiAlH4 (0.0002 mol) was added at 5° C. to a mixture of 3-{4-[1-(3-hydroxy-6-methyl-pyridin-2-ylmethyl)-4,6-dimethyl-1H-benzoimidazol-2-ylamino]-piperidin-1-yl}-propionic acid ethyl ester (r-1; 0.00009 mol; melting point: 172° C.) in tetrahydrofuran (10 ml) under N2 flow. The mixture was stirred at 5° C. for 1 hour, then at room temperature for 3 hours. A minimum of H2O and ethylacetate were added. The organic layer was separated, dried (over MgSO4), filtered and the solvent was evaporated until dryness. The residue was crystallized from 2-propanone/CH3CN/diisopropylether. The precipitate was filtered off and dried, yielding 0.026 g of 2-{2-[1-(3-hydroxy-propyl)-piperidin-4-ylamino]-4,6-dimethyl-benzoimidazol-1-ylmethyl}-6-methyl-pyridin-3-ol (r-2; 68%, melting point: 209° C.).

Workup

  1. waitat room temperature for 3 hours
  2. customThe organic layer was separated
  3. dry with materialdried (over MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated until dryness
  6. customThe residue was crystallized from 2-propanone/CH3CN/diisopropylether
  7. filtrationThe precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-ae4ccfb859d645a5bee7e0a34f2f91bc
Source dataset
uspto-grants-2014_11
Patent number
US08883837B2

Reaction notes

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