Borane;tetrahydrofuran → HCID 68685710, compound

HRID 1865486Notes

Reaction equation

HRID 1865486 reaction equation
[CH:1]1([CH2:4][S:5]([CH:8]2[CH2:13][CH2:12][C:11]([C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=O)([C:14]#[N:15])[CH2:10][CH2:9]2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.B.C1COCC1>>[CH:1]1([CH2:4][S:5]([CH:8]2[CH2:13][CH2:12][C:11]([CH2:14][NH2:15])([CH2:16][N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[CH2:10][CH2:9]2)(=[O:7])=[O:6])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68682712HCID 68682712, compound

Product 1

HCID 68685710HCID 68685710, compound

Procedure

4-cyclopropylmethanesulfonyl-1-(pyrrolidine-1-carbonyl)-cyclohexanecarbonitrile (246 mg; 0.0758 mmol) and borane-THF complex (1.0 M solution in THF; 10 ml; 10 mmol) were stirred at room temperature overnight. LC-MS indicated that the reaction had not gone to completion. The mixture was heated at reflux for 2 hours then allowed to cool to room temperature. The mixture was cooled in an icebath and quenched with MeOH (3 ml) then evaporated to dryness in vacuo. The residue was dissolved in MeOH (7 ml) and acidified with concentrated HCl. The mixture was stirred at room temperature for 18 hours. The mixture was poured on to a SCX cartridge. The cartridge was washed with several column lengths of MeOH followed by 2M ammonia in methanol solution to elute the amine. The desired product was obtained as a colourless oil upon evaporation of the appropriate fractions (44 mg). m/z=315 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe mixture was cooled in an icebath
  4. customquenched with MeOH (3 ml)
  5. customthen evaporated to dryness in vacuo
  6. dissolutionThe residue was dissolved in MeOH (7 ml)
  7. additionThe mixture was poured on to a SCX cartridge
  8. washThe cartridge was washed with several column lengths of MeOH
  9. washto elute the amine

Sources & evidence

ORD record
ord-8fe12cecf4594528ba57c456824124b3
Source dataset
uspto-grants-2009_12
Patent number
US07626056B2

Reaction notes

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