Dichloromethane → HCID 18187735, compound

HRID 278212Notes

Reaction equation

HRID 278212 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B1C2CCCC1CCC2.C[O-].[Na+].Br[C:30]1[CH:31]=[N:32][C:33]2[C:38]([CH:39]=1)=[CH:37][CH:36]=[CH:35][CH:34]=2.C(Cl)Cl>C1COCC1>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][CH:4]([CH2:1][CH2:2][CH2:3][C:30]2[CH:31]=[N:32][C:33]3[C:38]([CH:39]=2)=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:5][CH2:6]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 214133-BromoquinolineHCID 789669-Borabicyclo(3.3.1)nonaneHCID 10942334Sodium MethoxideHCID 11117722tert-Butyl 4-(prop-2-en-1-yl)piperidine-1-carboxylate

Product 1

HCID 18187735HCID 18187735, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(t-butoxycarbonyl)-4-(prop-2-en-1-yl)piperidine (from Procedure 5, Step B) (260 mg, 1.15 mmol) in THF (3 mL) under argon was treated with 0.5M 9-BBN solution in THF (2.30 mL, 1.15 mmol). The resulting mixture was stirred at rt for 2 h, then treated with sodium methoxide (68 mg, 1.25 mmol). The resulting mixture was stirred until it was homogeneous (˜15 min) and then was treated with 3-(bromo) quinoline (0.155 mL, 1.15 mmol) and [1,1′-bis(triphenylphosphino)ferrocene)dichloropalladium.methylene chloride (41 mg, 0.05 mmol). The resulting mixture was heated at reflux for 30 min, cooled and quenched with 1N NaOH (20 mL). The quenched reaction was extracted with 2×50 mL of ether; the extracts were dried over magnesium sulfate, combined and concentrated. FC (15 g of silica gel, 4:1 v/v hexanes/ethyl acetate) afforded the title compound (240 mg).

Workup

  1. stirringThe resulting mixture was stirred until it
  2. custom(˜15 min)
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux for 30 min
  5. temperaturecooled
  6. customquenched with 1N NaOH (20 mL)
  7. customThe quenched reaction
  8. extractionwas extracted with 2×50 mL of ether
  9. dry with materialthe extracts were dried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b7a2861018424fcfb6a89d53feba7c17
Source dataset
uspto-grants-2002_03
Patent number
US06358979B1

Reaction notes

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