Hydrochloric Acid → 1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester hydrochloride

HRID 634420Notes

Reaction equation

HRID 634420 reaction equation
[CH3:1][C:2]1([CH3:22])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH:10]=2)[O:3]1.[ClH:23]>CC(OC)(C)C.CCOCC>[ClH:23].[CH3:7][C:6]1([CH3:8])[C:2]([CH3:1])([CH3:22])[O:3][B:4]([C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH:10]=2)[O:5]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 497610841,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester hydrochlorideYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2 g, 6.47 mmol) was suspended in MTBE (8.1 mL) and 2M HCl in Et2O (24 mL). The reaction was stirred rt overnight, the white precipitate formed collected by filtration and washed with Et2O to give the title compound (1.434 g, 90%).

Workup

  1. customthe white precipitate formed
  2. filtrationcollected by filtration
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-76777c072ba54fb8bb2b8c2d6126188d
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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