Sodium hydride → Allyl-[(R)-6-(4-isopropyl-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid tert-butyl ester

HRID 870350Notes

Reaction equation

HRID 870350 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:19][CH:20]=[CH2:21])[C@@H:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[CH:36]([C:39]1[CH:44]=[CH:43][C:42]([S:45]([NH2:48])(=[O:47])=[O:46])=[CH:41][CH:40]=1)([CH3:38])[CH3:37].[H-].[Na+]>FC(F)(F)C1C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:19][CH:20]=[CH2:21])[C@@H:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:48][S:45]([C:42]3[CH:43]=[CH:44][C:39]([CH:36]([CH3:38])[CH3:37])=[CH:40][CH:41]=3)(=[O:46])=[O:47])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2323144-(1-Methylethyl)benzenesulfonamideHCID 68918871Allyl-((R)-6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester

Product 1

HCID 68919264Allyl-[(R)-6-(4-isopropyl-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid tert-butyl esterYield 115.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7368(Trifluoromethyl)benzeneSolvent2×

Procedure

In an inert atmosphere (argon), allyl-((R)-6-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (2.04 g, 5.5 mmol) was dissolved in trifluortoluol (10 ml) at room temperature. Tris(dibenzylideneacetone)dipalladium (230 mg, 0.25 mmol) and tri-tert-butyl-phosphane (152 mg, 0.75 mmol) were added to the reaction mixture. In a separate flask, 4-isopropyl-benzenesulfonamide (996 mg, 5 mmol) was dissolved in trifluortoluol (20 ml) at 65° C. Sodium hydride (50% in oil) (240 mg, 5 mmol) was added, stirred for 5 minutes and added to the reaction mixture. The reaction mixture was dispensed into 5 vials and stirred for 1 hour at 160° C. in the microwave (CEM). The combined reaction mixture was evaporated to dryness. H20 (50 ml) was added and extracted three times with 50 ml diethylether. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness to yield 2.8 g of crude product. The crude product was purified with silica gel chromatography with cyclohexane/ethyl acetate (85:15) as eluent, yielding the purified product (1.13 g, 45

Workup

  1. additionadded to the reaction mixture
  2. stirringstirred for 1 hour at 160° C. in the microwave (CEM)
  3. customThe combined reaction mixture
  4. customwas evaporated to dryness
  5. additionH20 (50 ml) was added
  6. extractionextracted three times with 50 ml diethylether
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-eaefb9f967c64ebca461fe087d37d75e
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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