Tetrahydrofuran → HCID 58654475, compound

HRID 1170464Notes

Reaction equation

HRID 1170464 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.[NH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:18])[O-:17].[CH2:19]1[CH2:23]OC[CH2:20]1.[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCOCC1.CC(O)=O.CO>[C:19]([O:18][C:16](=[O:17])[NH:15][CH2:14][CH2:13][NH:12][CH2:7][C:6]1[CH:1]=[CH:2][C:3]2[O:11][CH2:10][O:9][C:4]=2[CH:5]=1)([CH3:20])([CH3:23])[CH3:24]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 8438PiperonalHCID 5049666Sodium triacetoxyborohydrideHCID 21904494HCID 21904494, compound

Product 1

HCID 58654475HCID 58654475, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of piperonal (5.00 g, 33.3 mmol) and tert-butyl N-(2-aminoethylcarbamate (5.00 g, 31.2 mmol) in dry dioxane (70 mL) and AcOH (10 mL) was heated at 80° C. for 2 h. The solvent was evaporated prior to sequential addition of anhydrous THF (50 mL), MeOH (20 mL) and sodium triacetoxyborohydride (15.8 g, 74.5 mmol). The mixture was stirred for an additional 30 min then the solvent was removed under vacuum. NaOH solution (20% aqueous, w/w) was added to make the solution basic (pH 9), and the solution was extracted with EtOAc (150 mL). When the extracts were washed with brine, a precipitate formed in the funnel. It was filtered and dried to give 7.50 g (82%) of {2-[(benzo[1,3]dioxol-5-ylmethyl)-amino]-ethyl}-carbamic acid tert-butyl ester as a white solid.

Workup

  1. customThe solvent was evaporated
  2. customthe solvent was removed under vacuum
  3. additionNaOH solution (20% aqueous, w/w) was added
  4. extractionthe solution was extracted with EtOAc (150 mL)
  5. washWhen the extracts were washed with brine
  6. customa precipitate formed in the funnel
  7. filtrationIt was filtered
  8. customdried

Sources & evidence

ORD record
ord-821088bb83ee49fa90621ed602175370
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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