Sodium Hydroxide → HCID 57467286, compound

HRID 1044515Notes

Reaction equation

HRID 1044515 reaction equation
[CH:1]1([CH2:4][S:5]([NH:8][CH2:9][CH2:10][O:11][C:12]2[CH:21]=[C:20]3[C:15]([CH2:16][CH2:17][CH:18]([NH:30][C:31](=O)OCC)[CH:19]3[CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[CH:14][CH:13]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].CC(O)C.Cl>C1COCC1.C(Cl)Cl>[CH:1]1([CH2:4][S:5]([NH:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]3[CH2:16][CH2:17][CH:18]([NH:30][CH3:31])[CH:19]([CH2:22][C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)[C:20]=3[CH:21]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21912024Isopropanol hydrochlorideHCID 68514940HCID 68514940, compound

Product 1

HCID 57467286HCID 57467286, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The synthesis was performed starting from ethyl 7-(2-(cyclopropylmethylsulfonamido)-ethoxy)-1-(4-fluorobenzyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (synthesized in analogy to example 3), which was dissolved in THF (50 ml), after which LiAlH4 was added at room temperature and the mixture was stirred for 8 h under reflux. Addition of 2N aqueous NaOH, extraction with CH2Cl2, washing of the organic layers with saturated NaHCO3 solution and saturated NaCl solution and evaporation of the solvent gave a residue that was treated with iPrOH/HCl after which the product precipitated. After filtration a white salt (89 mg, 76%) was obtained.

Workup

  1. temperatureunder reflux
  2. washwashing of the organic layers with saturated NaHCO3 solution and saturated NaCl solution and evaporation of the solvent
  3. customgave a residue that
  4. customprecipitated
  5. filtrationAfter filtration a white salt (89 mg, 76%)
  6. customwas obtained

Sources & evidence

ORD record
ord-b88530586350434d8da586937eb11057
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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