Trifluoroacetic acid → 1,2,3,6-Tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

HRID 1947842Notes

Reaction equation

HRID 1947842 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([B:14]2[O:18][C:17]([CH3:20])([CH3:19])[C:16]([CH3:22])([CH3:21])[O:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:19][C:17]1([CH3:20])[C:16]([CH3:21])([CH3:22])[O:15][B:14]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)[O:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic 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 211054611,2,3,6-Tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (Tetrahedron Letters, 2000, 44, pp 3705-3708, 500 mg, 1.617 mmol) was added 2 mL DCM and 2 mL TFA. The mixture was stirred at room temperature for 3 hours. The solvents were evaporated in vacuo to afford the title compound (323 mg, 96% yield). The product was not further purified for next step. MS (ES+): m/z 210.19 (100) [MH+]; HPLC: tR=0.55 min (UPLC, Analytical).

Workup

  1. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-1d8edbd92eec481faf5ab3eb9006e2e5
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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