Acetic Acid → HCID 10410449, compound

HRID 392167Notes

Reaction equation

HRID 392167 reaction equation
O1C2C=CC=CC=2[C:3]([CH2:10][CH2:11][CH2:12][NH:13][CH2:14][C@@H:15]2[O:29][C:19]3=[C:20]4[C:25](=[CH:26][CH:27]=[C:18]3[O:17][CH2:16]2)[N:24]=[C:23]([CH3:28])[CH:22]=[CH:21]4)=C1.[CH:30](=[O:32])[CH3:31].C(O[BH-](O[C:43](=O)[CH3:44])OC(=O)C)(=O)C.[Na+].[C:47](O)(=O)[CH3:48]>O1CCCC1>[O:32]1[C:3]2[CH:10]=[CH:11][CH:12]=[CH:47][C:48]=2[C:31]([CH2:3][CH2:10][CH2:11][CH2:12][N:13]([CH2:43][CH3:44])[CH2:14][C@@H:15]2[O:29][C:19]3=[C:20]4[C:25](=[CH:26][CH:27]=[C:18]3[O:17][CH2:16]2)[N:24]=[C:23]([CH3:28])[CH:22]=[CH:21]4)=[CH:30]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69365117HCID 69365117, compound

Product 1

HCID 10410449HCID 10410449, compoundYield 108.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[3-(1-benzofuran-3-yl)propyl]-N-{[(2S)-8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}amine (206 mg, 0.512 mmol) in anhydrous tetrahydrofuran (3 mL) was added acetaldehyde (206 μL, 3.67 mmol), sodium triacetoxyborohydride (445 mg, 2.1 mmol), and glacial acetic acid (41 μL, 0.716 mmol). The reaction was allowed to stir at ambient temperature overnight, then was quenched with 1 M aqueous sodium hydroxide (5 mL) and diluted with water (10 mL). The aqueous mixture was extracted with methylene chloride (3×25 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography on silica gel (50/45/5 ethyl acetate/hexane/triethylamine) afforded 120 mg (55%) of the title compound as an orange oil, which was converted to its fumarate salt as a brown solid: mp 87-92° C.; MS (ES) m/z 431 [M+H]+; [α]D −8.58° (c 1.0, DMSO).

Workup

  1. customwas quenched with 1 M aqueous sodium hydroxide (5 mL)
  2. additiondiluted with water (10 mL)
  3. extractionThe aqueous mixture was extracted with methylene chloride (3×25 mL)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8036c3394a5046068857feb510047e92
Source dataset
uspto-grants-2004_10
Patent number
US06800637B2

Reaction notes

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