Ethyl Acetate → HCID 22054582, compound

HRID 1829751Notes

Reaction equation

HRID 1829751 reaction equation
[Li].[CH3:2][C:3]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:10]2[C:5](=[CH:6][C:7]([C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=O)=[CH:8][CH:9]=2)[N:4]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].C(OCC)(=O)C>O1CCCC1>[CH3:2][C:3]1[CH:12]=[C:11]([N:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[C:10]2[C:5](=[CH:6][C:7]([CH2:18][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:8][CH:9]=2)[N:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 3028194LithiumHCID 9855836Potassium sodium tartarateHCID 22054545HCID 22054545, compound

Product 1

HCID 22054582HCID 22054582, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminumhydride (20 mg, 0.52 mmol) was added to a solution of (2-methyl-4-pyrrolidin-1-yl-quinolin-7-yl)-pyrrolidin-1-yl-methanone (example 27, 80 mg, 0.26 mmol) in tetrahydrofuran (1 mL), and the reaction mixture was stirred at room temperature for 3 h, then 1 M aq. potassium sodium tartrate solution (10 mL) and ethyl acetate (10 mL) were added. After 15 min, the organic layer was separated, washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, dichloromethane/methanol 9:1) afforded the title compound (31 mg, 41%). Off-white solid, ISP-MS: m/e=337.3 ([M+H]+).

Workup

  1. waitAfter 15 min
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-bf6fdd05872e410fa781689ed27bf56d
Source dataset
uspto-grants-2006_06
Patent number
US07064134B2

Reaction notes

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