Hydrochloric Acid → 4,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochloride

HRID 1526446Notes

Reaction equation

HRID 1526446 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[O:14][CH:15]=[CH:16][C:10]=2[CH2:9]1)=O)(C)(C)C.[ClH:17]>CO>[ClH:17].[O:14]1[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]=2[CH:16]=[CH:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 196002415-Boc-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

Product 1

HCID 195999414,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 6,7-dihydro-4H-furo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (0.56 g, 2.51 mmol) in methanol (50 mL) was added concentrated hydrochloric acid solution (37%, 1.4 mL). The mixture stirred at room temperature for 5.5 hours, monitored by TLC. The methanol was evaporated under reduced pressure to yield 4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride (0.5 g, 100% yield) as a yellow powder. 1H NMR (Field: 300 MHz, Solvent: CD3OD/TMS) δ (ppm): 7.47 (s, 1H), 6.42 (s, 1H), 4.20 (s, 2H), 3.57 (m, 2H), 3.03 (m, 2H). 13C NMR (Field: 75 MHz, Solvent: CDCl3/TMS) δ (ppm): 147.23, 143.89, 112.23, 109.50, 43.10, 42.37, 21.70.

Workup

  1. customThe methanol was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b0cd198efaa345ad9551c16b8a432212
Source dataset
uspto-grants-2015_07
Patent number
US09085585B2

Reaction notes

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