Lithium Chloride → HCID 17854298, compound

HRID 218760Notes

Reaction equation

HRID 218760 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-b0e6f04b8cc449778bba57750d1d0e43
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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