Lithium Chloride → HCID 17854298, compound

HRID 2265531Notes

Reaction equation

HRID 2265531 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH:14]2[C:19]([N:21]([CH2:31][C:32]1[CH:33]=[N:34][N:35]([CH2:37][C:38](OCC)=[O:39])[CH:36]=1)[C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=1)=[O:20])C1C=CC=CC=1.[Cl-].[Li+].[BH4-].[Na+]>O1CCCC1.C(O)C>[OH:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH:14]2[C:19]([N:21]([CH2:31][C:32]1[CH:33]=[N:34][N:35]([CH2:37][CH2:38][OH:39])[CH:36]=1)[C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=1)=[O:20]

Participants

5

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 67183885HCID 67183885, compound

Product 1

HCID 17854298HCID 17854298, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Ethyl 2-(4-{[N-(5-benzyloxy-1,2,3,4-tetrahydronaphthalen-1-ylcarbonyl)-N-(4-isopropylphenyl)amino]methyl}pyrazol-1-yl)acetate (1.0 g) was dissolved in tetrahydrofuran:ethanol (1:2) solution (10 mL), and lithium chloride (0.30 g) and sodium borohydride (0.27 g) were added. The mixture was stirred at room temperature for 3 hr. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the obtained residue (0.91 g) was reacted and treated in the same manner as in Example 17 to give 5-hydroxy-N-{[1-(2-hydroxyethyl)pyrazol-4-yl]methyl}-N-(4-isopropylphenyl)-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.25 g). melting point: 110-114° C.

Workup

  1. additionwere added
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue (0.91 g) was reacted
  7. additiontreated in the same manner as in Example 17

Sources & evidence

ORD record
ord-1bc770b4b9e44b31b439b5b90e5ac125
Source dataset
uspto-grants-2010_12
Patent number
US07855297B2

Reaction notes

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