Cesium carbonate → tert-Butyl [1-(4-chlorobenzyl)-7-{3-[(propylsulfonyl)amino]propyl}-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

HRID 2177102Notes

Reaction equation

HRID 2177102 reaction equation
B1C2CCCC1CCC2.[CH2:10]([NH:13][S:14]([CH2:17][CH2:18][CH3:19])(=[O:16])=[O:15])[CH:11]=[CH2:12].FC(F)(F)S(O[C:26]1[CH:35]=[CH:34][C:33]2[CH2:32][CH2:31][CH:30]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:29]([CH2:44][C:45]3[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=3)[C:28]=2[CH:27]=1)(=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[C:40]([O:39][C:37](=[O:38])[NH:36][CH:30]1[CH2:31][CH2:32][C:33]2[C:28](=[CH:27][C:26]([CH2:12][CH2:11][CH2:10][NH:13][S:14]([CH2:17][CH2:18][CH3:19])(=[O:16])=[O:15])=[CH:35][CH:34]=2)[CH:29]1[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=1)([CH3:43])([CH3:41])[CH3:42]

Participants

10

Reactant 5

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 789669-Borabicyclo(3.3.1)nonaneHCID 237363N-allylpropane-1-sulfonamideHCID 574672047-(Tert-butoxycarbonylamino)-8-(4-chlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 59547819tert-Butyl [1-(4-chlorobenzyl)-7-{3-[(propylsulfonyl)amino]propyl}-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 9-BBN (0.5 M in tetrahydrofuran, 8.85 mL, 4.42 mmol) was added dropwise a solution N-allylpropane-1-sulfonamide (1152 mg, 7.06 mmol) in tetrahydrofuran (1 mL) a 0° C. After stirring at 0° C. to 5° C. for 3.5 hours dioxane (25 mL) was added followed by 7-(tert-butoxycarbonylamino)-8-(4-chlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (1000 mg, 1.923 mmol, prepared analogously to example 34.3), palladium acetate (43.2 mg, 0.192 mmol), triphenylphosphine (101 mg, 0.385 mmol) and cesium carbonate (1253 mg, 3.85 mmol). The yellow reaction mixture was heated under reflux for 3 hours. The reaction mixture was diluted with ethyl acetate (60 mL) and washed with water (2×40 mL). The organic layer was dried and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloro methane, methanol).

Workup

  1. additionwas added
  2. temperatureThe yellow reaction mixture was heated
  3. temperatureunder reflux for 3 hours
  4. washwashed with water (2×40 mL)
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (silica gel, dichloro methane, methanol)

Sources & evidence

ORD record
ord-2f2b25dfe34341289ee72060272557e9
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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