Chlorotrimethylsilane → HCID 67287340, compound

HRID 1626515Notes

Reaction equation

HRID 1626515 reaction equation
[BH4-].[Li+].Cl[Si](C)(C)C.[CH:8]1([C:11]2[N:16]=[C:15]([O:17][CH3:18])[C:14](/[CH:19]=[CH:20]/[N+:21]([O-])=O)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1>C1COCC1>[CH:8]1([C:11]2[N:16]=[C:15]([O:17][CH3:18])[C:14]([CH2:19][CH2:20][NH2:21])=[CH:13][CH:12]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 67288800HCID 67288800, compound

Product 1

HCID 67287340HCID 67287340, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of lithium borohydride (1226 μL, 2.45 mmol) in THF was added chlorotrimethylsilane (622 μl, 4.90 mmol) dropwise. After stirring for 15 minutes, argon was bubbled through the reaction mixture for 2 minutes to eliminate any trimethylsilane in the reaction mixture. (E)-6-cyclopropyl-2-methoxy-3-(2-nitrovinyl)pyridine (135 mg, 0.613 mmol) was added (in 1 mL of THF). The reaction was heated to reflux for 2 hours, cooled to 0° C. and carefully quenched with methanol (1 mL). The reaction mixture was concentrated, diluted with dichloromethane and 20% aqueous KOH. The layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated to yield 2-(6-cyclopropyl-2-methoxypyridin-3-yl)ethanamine (118 mg, 0.614 mmol, 100% yield).

Workup

  1. customargon was bubbled through the reaction mixture for 2 minutes
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 2 hours
  4. customcarefully quenched with methanol (1 mL)
  5. concentrationThe reaction mixture was concentrated
  6. additiondiluted with dichloromethane and 20% aqueous KOH
  7. customThe layers were separated
  8. dry with materialthe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-63fa5efeda2f4aa990163bc3c85414f6
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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