Borane → HCID 67087005, compound

HRID 1665149Notes

Reaction equation

HRID 1665149 reaction equation
[NH2:1][C@H:2]([CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si](C(C)(C)C)(C)C)=[CH:11][CH:10]=1)[C:3]([NH2:5])=O.B>C1COCC1.CO>[NH2:1][C@@H:2]([CH2:3][NH2:5])[CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 6331Borane3×HCID 67087069HCID 67087069, compound

Product 1

HCID 67087005HCID 67087005, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
5 °C

Procedure

A solution of (R)-2-Amino-5-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-pentanoic acid amide (7.74 g, 24 mmol) in THF is stirred at 5° C. and borane (96 ml of a 1 M solution in THF, 96 mmol) is added. The mixture is stirred at 5° C. until a homogeneous mixture is obtained and then stirred at room temperature for 30 minutes and 35° C. for 3 hours. After this time, further borane (24 ml of a 1 M solution in THF, 24 mmol) is added and the reaction is heated at 35° C. for 18 hours. After this time, a further portion of borane (24 ml of a 1 M solution in THF, 24 mmol) is added and the reaction heated at 35° C. for a further 24 hours. After this time, the reaction is cooled to 10° C., and quenched by adding dropwise to MeOH (50 ml) at −5° C. After allowing to warm to room temperature the solvent is removed in vacuo to afford a yellow oil. The oil is dissolved in MeOH (250 ml) and SCX-2 silica (180 g, 0.63 mmol/g, 120 mmol) is added. The silica suspension is shaken for 18 hours, the silica is removed by filtration, washed with MeOH (3×100 ml), then suspended in 7M NH3 in MeOH and shaken for 18 hours. The silica is removed by filtration and the 7M NH3 in MeOH is removed in vacuo to afford the title compound as a yellow oil; [M+H]+ 195

Workup

  1. customis obtained
  2. stirringstirred at room temperature for 30 minutes and 35° C. for 3 hours
  3. temperaturethe reaction is heated at 35° C. for 18 hours
  4. temperaturethe reaction heated at 35° C. for a further 24 hours
  5. temperatureAfter this time, the reaction is cooled to 10° C.
  6. customquenched
  7. additionby adding dropwise to MeOH (50 ml) at −5° C
  8. temperatureto warm to room temperature the solvent
  9. customis removed in vacuo
  10. customto afford a yellow oil
  11. additionSCX-2 silica (180 g, 0.63 mmol/g, 120 mmol) is added
  12. stirringThe silica suspension is shaken for 18 hours
  13. customthe silica is removed by filtration
  14. washwashed with MeOH (3×100 ml)
  15. stirringshaken for 18 hours
  16. customThe silica is removed by filtration
  17. customthe 7M NH3 in MeOH is removed in vacuo

Sources & evidence

ORD record
ord-be92a38da12b406e9f5f1ec90d31bdf3
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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