2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde → HCID 21104706, compound

HRID 1354232Notes

Reaction equation

HRID 1354232 reaction equation
[NH2:1][CH2:2][C:3]1[CH2:8][N:7]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5][CH:4]=1.[O:17]1[C:22]2[CH:23]=[CH:24][C:25]([CH:27]=O)=[CH:26][C:21]=2[O:20][CH2:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.ClCCCl>[O:17]1[C:22]2[CH:23]=[CH:24][C:25]([CH2:27][NH:1][CH2:2][C:3]3[CH2:8][N:7]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5][CH:4]=3)=[CH:26][C:21]=2[O:20][CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69519174HCID 69519174, compound

Product 1

HCID 21104706HCID 21104706, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 5-aminomethyl-3,6-dihydro-2H-pyridine-1-carbamate (0.7 g, 3.3 mmol) and 1,4-benzodioxane-6-carbaldehyde (0.54 g, 3.3 mmol) in THF (2 ml) and DCE (4 ml) was stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (0.770 g, 3.81 mmol) was then added thereto. The reaction mixture was stirred at room temperature for 5 hours and filtered through Hydromatrix (wetted with saturated NaHCO3 solution) and the filtrate was concentrated. The residue was purified by chromatography on silica gel (EtOAc/hex 2/1 and then EtOAc/MeOH 9/1).

Workup

  1. filtrationfiltered through Hydromatrix (wetted with saturated NaHCO3 solution)
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by chromatography on silica gel (EtOAc/hex 2/1

Sources & evidence

ORD record
ord-8514ee5692764eb7bb265066a4284592
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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