HCID 90134886, compound → [(3S)-2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]methanamine

HRID 1483028Notes

Reaction equation

HRID 1483028 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:14][C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[O:7][CH2:6]1)=[N+]=[N-]>CO.[Pd]>[O:7]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[O:14][C@@H:5]([CH2:4][NH2:1])[CH2:6]1

Participants

4

Reactant 1

HCID 90134886HCID 90134886, compound

Product 1

HCID 68531823[(3S)-2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl]methanamineYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve (3S)-3-(azidomethyl)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine (7.5 g, 39.03 mmol) in MeOH (390 mL). Degas the mixture by subjecting it to reduced pressure then back filling with nitrogen (3×); add 10% Pd/C (2.08 g, 1.95 mmol); and again degas the mixture. Stir the resulting degassed mixture at ambient temperature under a hydrogen atmosphere for 17 hours. Filter the resulting mixture through Celite® and remove solvents of the filtrate under reduced pressure to provide the title compound (6.5 g, 100%) as an oil. MS (m/z): 167 (M+1).

Workup

  1. customDegas the mixture
  2. customand again degas the mixture
  3. customdegassed mixture at ambient temperature under a hydrogen atmosphere for 17 hours
  4. filtrationFilter the resulting mixture through Celite®
  5. customremove solvents of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-40bcf2a8a5cd40ac9b7b21c8885c8398
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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