Water → HCID 68932519, compound

HRID 1510696Notes

Reaction equation

HRID 1510696 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[O:15]1[C:24]2[CH:23]=[C:22]([CH:25]=O)[N:21]=[CH:20][C:19]=2[O:18][CH2:17][CH2:16]1.[BH4-].[Na+].O>CO.ClCCl>[O:15]1[C:24]2[CH:23]=[C:22]([CH2:25][NH:1][CH2:2][CH:3]3[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]3)[N:21]=[CH:20][C:19]=2[O:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 962WaterHCID 2756485tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylateHCID 4311764Sodium borohydrideHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde

Product 1

HCID 68932519HCID 68932519, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.28 g of tert-butyl 3-(aminomethyl)pyrrolidine-1-carboxylate in a mixture of 7 mL of methanol and 20 mL of dichloromethane, 0.23 g of 2,3-dihydro(1,4)dioxino(2,3-c)pyridine-7-carbaldehyde and 0.50 g of molecular sieves 3A were added, the mixture was stirred at room temperature for 3 hours, and then, the reaction mixture was charged with 79 mg of sodium borohydride and stirred at room temperature for 5 hours 30 minutes. Thereto was added water under cooling with ice, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.48 g of tert-butyl 3-(((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)methyl)pyrrolidine-1-carboxylate as a colorless oily substance.

Workup

  1. additionwere added
  2. stirringstirred at room temperature for 5 hours 30 minutes
  3. temperatureunder cooling with ice
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with chloroform
  6. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-625c4794b3de48b2a839c5816e253f1c
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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