Hydrochloric Acid → HCID 131735119, compound

HRID 2207713Notes

Reaction equation

HRID 2207713 reaction equation
C(OC([N:8]([CH2:16][C@H:17]([C:19]1[CH:24]=[CH:23][N:22]=[C:21]2[O:25][CH2:26][CH2:27][O:28][C:20]=12)[CH3:18])C(=O)OC(C)(C)C)=O)(C)(C)C.[ClH:29].CC(O)C>CCO>[ClH:29].[ClH:29].[O:28]1[C:20]2[C:21](=[N:22][CH:23]=[CH:24][C:19]=2[C@H:17]([CH3:18])[CH2:16][NH2:8])[O:25][CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 86699657HCID 86699657, compound

Product 1

HCID 131735119HCID 131735119, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

As shown in step 7-iv of Scheme 7, (S)-tert-butyl N-tert-butoxycarbonyl-N-[2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl]carbamate (7.74 g, 39.8 mmol) was dissolved in EtOH, HCl in IPA (60 mL of 4 M solution, 240 mmol) was added and the reaction mixture was refluxed for 1 hour. The reaction mixture was concentrated under reduced pressure to a minimum volume, Et2O was added, and the resulting suspension stirred for 16 hours. The solid was collected by filtration and dried under high vacuum to provide (S)-2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propan-1-amine, dihydrochloride as a yellowish solid (Compound 2025, 10.55 g, 100% yield): 1H NMR (300 MHz, CDCl3) δ 7.80 (d, 1H), 7.10 (d, 1H), 4.50 (m, 2H), 4.40 (m, 2H), 3.40 (m, 1H), 3.00 (m, 2H), 1.25 (d, 3H).

Workup

  1. temperaturethe reaction mixture was refluxed for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure to a minimum volume, Et2O
  3. additionwas added
  4. filtrationThe solid was collected by filtration
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-0f2a7d204c2546ed985ab35eae1b893c
Source dataset
uspto-grants-2016_06
Patent number
US09376448B2

Reaction notes

Loading…