2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde → Tert-butyl (1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-piperidin-4-yl)carbamate

HRID 2193091Notes

Reaction equation

HRID 2193091 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[C:13]([O:17][C:18](=[O:26])[NH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([CH3:16])([CH3:15])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[C:13]([O:17][C:18](=[O:26])[NH:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:11][C:9]2[CH:8]=[CH:7][C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]=3[CH:10]=2)[CH2:22][CH2:21]1)([CH3:16])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86669946Tert-butyl (1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-piperidin-4-yl)carbamateYield 64.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

To 20 mL of a chloroform solution containing 2.17 g of 1,4-benzodioxane-6-carbaldehyde and 2.67 g of tert-butyl(piperidin-4-yl)carbamate, 0.76 mL of acetic acid was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was added with 4.27 g of sodium triacetoxyborohydride, and stirred overnight. Thereto was added an aqueous saturated sodium hydrogen carbonate solution, and the organic layer was separated. The organic layer was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate:hexane=5:1] to obtain 2.96 g of tert-butyl(1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-piperidin-4-yl)carbamate.

Workup

  1. additionwas added
  2. stirringstirred overnight
  3. customthe organic layer was separated
  4. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; ethyl acetate:hexane=5:1]

Sources & evidence

ORD record
ord-cb427df8c127434f9c9684400a4a7c03
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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