Sodium Hydroxide → HCID 57471286, compound

HRID 2177098Notes

Reaction equation

HRID 2177098 reaction equation
[CH2:1]([CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][NH:21][S:22]([CH2:25][CH:26]3[CH2:28][CH2:27]3)(=[O:24])=[O:23])[CH:16]=2)[CH2:11][CH2:10][CH:9]1[NH:29][C:30](=O)OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].CC(O)C.[ClH:47]>C1COCC1.C(Cl)Cl>[ClH:47].[CH2:1]([CH:8]1[C:17]2[CH:16]=[C:15]([O:18][CH2:19][CH2:20][NH:21][S:22]([CH2:25][CH:26]3[CH2:28][CH2:27]3)(=[O:24])=[O:23])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10][CH:9]1[NH:29][CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21912024Isopropanol hydrochlorideHCID 57471304HCID 57471304, compound

Product 1

HCID 57471286HCID 57471286, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The synthesis was performed starting from ethyl 1-benzyl-7-(2-(cyclopropylmethylsulfonamido)ethoxy)-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 (287 mg, 58%) were 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 (287 mg, 58%)
  6. customwere obtained

Sources & evidence

ORD record
ord-0302abd24816409bb2bfc11f2ccc0f34
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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