Sodium Hydroxide → HCID 15884728, compound

HRID 379517Notes

Reaction equation

HRID 379517 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])[NH:5]1.[CH3:17][C:18]([O-:20])=O.[Na+].[BH-](O[C:32]([CH3:34])=[O:33])(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C(Cl)Cl.O>[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])[N:5]1[CH2:3][CH2:4][N:5]1[C:18](=[O:20])[C:17]2=[CH:9][CH:6]=[CH:7][CH:8]=[C:34]2[C:32]1=[O:33]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 15884727HCID 15884727, compound

Product 1

HCID 15884728HCID 15884728, compoundYield 173%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxymethyl-5-(2-methoxyphenyl)-tetrahydropyrrole (226 mg, 1.02 mmol) in CH2Cl2 was added NaOAc (88 mg, 1.07 mmol), N-phthalimidoacetaldehyde (203 mg, 1.07 mmol) and NaB(OAc)3H (326 mg, 1.54 mmol) and the resulting suspension was stirred at ambient temperature for 17 hours. H2O was added followed by 1N NaOH until pH was 10, the aqueous layer was extracted with CHCl3 (×4), and the combined organic layers were washed with brine, dried over MgSO4 and evaporated in vacuo. The crude product was purified by silica gel flash chromatography (5% MeOH-0.5% NH3.H2O-94.5% CH2Cl2) to afford the title compound as a yellow oil (348 mg, 86%). MS m/z: 395 (M+H)

Workup

  1. extractionthe aqueous layer was extracted with CHCl3 (×4)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by silica gel flash chromatography (5% MeOH-0.5% NH3.H2O-94.5% CH2Cl2)

Sources & evidence

ORD record
ord-be3da1c501c64cc387bd3c62b206b635
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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