Triethylsilane → HCID 178515018, compound

HRID 1631432Notes

Reaction equation

HRID 1631432 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.C([SiH](CC)CC)C.[CH:33]1([CH:36]=O)[CH2:35][CH2:34]1>C(#N)C.Br[Bi](Br)Br>[CH:33]1([CH2:36][O:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([N:15]3[C:16](=[O:25])[C:17]4[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:23]3=[O:24])[CH2:11][CH2:10]2)[CH2:35][CH2:34]1

Participants

6

Reactant 3

HCID 12052TriethylsilaneHCID 123114CyclopropanecarboxaldehydeHCID 178455354HCID 178455354, compound

Product 1

HCID 178515018HCID 178515018, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 82232bismuth(III) bromideCatalystHCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 12B (750 mg, 2.086 mmol) in acetonitrile (10 mL) was treated with triethylsilane (0.432 mL, 2.71 mmol) and tribromobismuthine (94 mg, 0.209 mmol), followed by slow addition of cyclopropanecarbaldehyde (175 mg, 2.503 mmol) (dissolved in acetonitrile (0.5 mL)). The reaction mixture was stirred at room temperature overnight. The dark solid was removed by filtration, the filtrate was concentrated, and the residue was purified by ISCO silica column (24 g), gradient elution with ethyl acetate:hexane (0%-100% ethyl acetate over 15 min). Concentration of the desired fractions yielded 12C (630 mg, 2.104 mmol, >quantitative yield) as a white solid. MS (ES): m/z=322 [M+Na]+. 1H NMR (400 MHz, CDCl3) δ ppm 7.56-7.65 (m, 2H); 7.46-7.53 (m, 2H); 3.89-3.99 (m, 1H); 3.13-3.22 (m, 1H); 3.12 (d, 2H, J=6.8 Hz); 2.04-2.16 (m, 2H); 1.92-2.00 (m, 2H); 1.52-1.61 (m, 2H); 1.14-1.27 (m, 2H); 0.80-0.92 (m, 1H); 0.30-0.39 (m, 2H); −0.02-0.05 (m, 2H).

Workup

  1. customThe dark solid was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by ISCO silica column (24 g), gradient elution with ethyl acetate
  4. customhexane (0%-100% ethyl acetate over 15 min)

Sources & evidence

ORD record
ord-5148fdb928f8419db5a93b8621ebbe63
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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