Water → HCID 17861996, compound

HRID 2109330Notes

Reaction equation

HRID 2109330 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]([O:5][C:6]1(O)[CH:15]=[CH:14][C:13]2[CH:12]([CH2:16][C:17](OCC)=[O:18])[N:11]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:10][CH2:9][C:8]=2[CH2:7]1)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:30][N:2]([CH3:1])[C:3]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]([CH2:16][CH2:17][OH:18])[N:11]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:10][CH2:9]2)=[O:4]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68819021HCID 68819021, compound

Product 1

HCID 17861996HCID 17861996, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of t-butyl 6-dimethylcarbamoyloxy-1-ethoxycarbonylmethyl-6-hydroxy-3,4-dihydro-1H-isoquinoline-2-carboxylate (1.97 g, 4.84 mmol) synthesized in step (e) of Example 187 in tetrahydrofuran (30 ml) was added lithium aluminum hydride (270 mg, 7.2 mmol) at −78° C., and the resulting mixture was stirred for 20 minutes at −78° C. and for 20 minutes at 0° C. successively under a nitrogen atmosphere. After stirring, to the reaction mixture were added water (0.3 ml), 15% aqueous sodium hydroxide solution (0.3 ml) and water (0.9 ml) in this order with stirring, and the resulting mixture was dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to afford the crude product. The crude product was purified by chromatography on a silica gel column using a mixed solvent of hexane and. ethyl acetate (1:1-0:1) as the eluent to afford the title compound (1.38 g, yield: 78%) as a colorless oil.

Workup

  1. stirringAfter stirring, to the reaction mixture
  2. stirringwith stirring
  3. dry with materialthe resulting mixture was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford the crude product
  7. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-49fc25e11db04218ad19e0cd9112a439
Source dataset
uspto-grants-2009_04
Patent number
US07514475B2

Reaction notes

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