(Dimethyl sulfide)trihydroboron → (+,-) Trans Propane-2-sulfonic Acid {2-[4'-(2-amino-ethyl)-biphenyl-4-yl]-cyclopentyl}-amide

HRID 989493Notes

Reaction equation

HRID 989493 reaction equation
[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C@@H:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)#[N:2].CSC.B>C1COCC1>[NH2:2][CH2:1][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C@@H:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 69112880(+,-) Trans Propane-2-sulfonic Acid [2-(4'-cyanomethyl-biphenyl-4-yl)-cyclopentyl]-amide

Product 1

HCID 69112967(+,-) Trans Propane-2-sulfonic Acid {2-[4'-(2-amino-ethyl)-biphenyl-4-yl]-cyclopentyl}-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(+,−) Trans propane-2-sulfonic acid [2-(4′-cyanomethyl-biphenyl-4-yl)-cyclopentyl]-amide (210 mg, 0.55 mmol, prepared in example 8) was dissolved in 20 mL dry THF. To this solution was added 0.83 mL (1.65 mmol) of a 2.0 M solution of borane dimethyl sulfide in THF. The reaction was heated to reflux for 4 hours then concentrated in vacuo. To this solid was added 30 mL of diethyl ether, 15 mL of concentrated HCl, 10 mL of water, and 5 mL of methanol and stirred at room temperature for 30 minutes. The aqueous layer was separated, and the organic phase washed 1× with water. The combined aqueous phases were made basic with sodium hydroxide at 0° C. and extracted into diethyl ether (2×50 mL) followed by ethyl acetate (1×50 mL). The combined organic phases were dried over sodium sulfate, filtered, and concentrated to a crude oil which was used without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 hours
  3. concentrationthen concentrated in vacuo
  4. additionTo this solid was added 30 mL of diethyl ether, 15 mL of concentrated HCl, 10 mL of water, and 5 mL of methanol
  5. customThe aqueous layer was separated
  6. washthe organic phase washed 1× with water
  7. customwere made basic with sodium hydroxide at 0° C.
  8. extractionextracted into diethyl ether (2×50 mL)
  9. dry with materialThe combined organic phases were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated to a crude oil which
  12. customwas used without further purification

Sources & evidence

ORD record
ord-d2712f65df724e66bac8d9438da09ba7
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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