Triethylamine → HCID 58036797, compound

HRID 1028360Notes

Reaction equation

HRID 1028360 reaction equation
[C:1]1([P:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[NH:17][CH:16]([CH3:19])[CH2:15][CH2:14]3)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.Cl[SiH](Cl)Cl.[OH-].[Na+]>C(Cl)Cl>[C:20]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[NH:17][CH:16]([CH3:19])[CH2:15][CH2:14]3)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24811TrichlorosilaneHCID 58036792HCID 58036792, compound

Product 1

HCID 58036797HCID 58036797, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-diphenylphosphinoyl-2-methyl-1,2,3,4-tetrahydroquinoline (6) (1.5 g, 4.5 mmol) in dry degassed toluene (40 mL) was added degassed Et3N (3.15 mL, 22.5 mmol) followed by trichlorosilane (2.25 mL, 22.5 mmol). The mixture was stirred at 80° C. for 30 minutes before cautiously adding 2N NaOH (150 mL) and cooling down to room temperature. Products were then extracted with EtOAc, washed with water and saturated aqueous NaCl, dried (MgSO4) and evaporated to give a yellow oil. This oil was taken up in CH2Cl2 (100 mL), and filtered over silica gel (˜25 mL) eluting with further portions of CH2Cl2 (4×100 mL). The combined filtrates were then evaporated to give compound 7 (1.2 g) as a light yellow oil in 80% yield. 1H NMR (400.13 MHz, CDCl3) δ 7.4-7.3 (m, 10H, Ph-H), 6.99 (d, 1H, J=7.2 Hz, C5—H), 6.62 (ddd, 1H, J=7.2, 6.0, 1.2 Hz, C7—H), 6.52 (t, 1H, J=7.6 Hz, C6—H), 4.65 (bs, 1H, N1—H), 3.4-3.3 (m, 1H, C2—H), 2.9-2.7 (m, 2H, C4a/b—H), 2.0-1.9 (m, 1H, C3a—H), 1.6-1.5 (m, 1H, Cab—H), 1.11 (d, 3H, J=6.4 Hz, C1′—CH3) ppm; 13C NMR (100.61 MHz, CDCl3) δ 147.9 (d, J=18.2 Hz), 147.7 (d, J=18.2 Hz), 136.1 (d, J=12.1 Hz), 136.0 (d, J=13.1 Hz), 135.8 (d, J=13.1 Hz), 135.7 (d, J=13.1 Hz), 134.1-133.5 (m), 132.5 (d, J=12.1 Hz), 132.4 (d, J=12.1 Hz), 130.5, (d, J=13.1 Hz), 12 8.7-128.4 (m), 120.7 (d, J=12.1 Hz), 117.0, (d, J=12.1 Hz), 116.3 (d, J=12.1 Hz), 47.4, 39.6, 26.8, 22.4 ppm; 31P NMR (161.97 MHz, CDCl3) δ −21.9 ppm.

Workup

  1. customdegassed toluene (40 mL)
  2. additionwas added
  3. temperaturecooling down to room temperature
  4. extractionProducts were then extracted with EtOAc
  5. washwashed with water and saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give a yellow oil
  9. filtrationfiltered over silica gel (˜25 mL)
  10. washeluting with further portions of CH2Cl2 (4×100 mL)
  11. customThe combined filtrates were then evaporated

Sources & evidence

ORD record
ord-734013e13b8340cf85d7d12c9eaf5622
Source dataset
uspto-grants-2014_05
Patent number
US08735583B2

Reaction notes

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