Dichloromethane → HCID 18187735, compound

HRID 1862657Notes

Reaction equation

HRID 1862657 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, compound

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 ml).

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-abb6e01edd3444058f52c547aac48b59
Source dataset
uspto-grants-2003_03
Patent number
US06538002B1

Reaction notes

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