Methyl iodide → HCID 69289956, compound

HRID 2415501Notes

Reaction equation

HRID 2415501 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:20]3[CH2:24][CH2:23][C@@H:22]([OH:25])[CH2:21]3)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26]C(C)([O-])C.[K+].CI>C1COCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:20]3[CH2:24][CH2:23][C@@H:22]([O:25][CH3:26])[CH2:21]3)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 23665647Potassium tert-butoxide2×HCID 69288172HCID 69288172, compound

Product 1

HCID 69289956HCID 69289956, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3.2 g (9.5 mmol) of (R)-1-(7-benzyloxy-2-methyl-quinolin-4-yl)-pyrrolidin-3-ol, product of example 86, in THF (275 ml) was treated at RT under nitrogen with 1.42 g (12.4 mmol) of potassium tert-butoxide. The suspension was stirred for 20 minutes at RT then 0.72 ml (11.4 mmol) of methyl iodide were added. After 25 minutes of stirring further 0.284 g (2.48 mmol) of potassium tert-butoxide were added followed by 0.144 ml (2.28 mol) of methyl iodide (10 minutes later) for completion of the reaction. Stirring was continued for 20 minutes, the reaction mixture was then concentrated in vacuo and the residue partitioned between water and AcOEt. The layers were separated the aqueous layer once extracted with AcOEt, the combined organic layers washed with brine, dried over magnesium sulphate and concentrated in vacuo to give 3.33 g (94.5%) (R)-7-benzyloxy-4-(3-methoxy-pyrrolidin-1-yl)-2-methyl-quinoline as an orange viscous oil. ISP mass spectrum, m/e: 349.5 (M+1 calculated for C22H24FN2O2: 349).

Workup

  1. additionwere added
  2. custom10 minutes
  3. customfor completion of the reaction
  4. stirringStirring
  5. waitwas continued for 20 minutes
  6. concentrationthe reaction mixture was then concentrated in vacuo
  7. customthe residue partitioned between water and AcOEt
  8. customThe layers were separated the aqueous layer
  9. extractiononce extracted with AcOEt
  10. washthe combined organic layers washed with brine
  11. dry with materialdried over magnesium sulphate
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf156bb43dad423fb76e989682e3c073
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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