1-Phenylpyrrolidine → 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrrolidine

HRID 1490491Notes

Reaction equation

HRID 1490491 reaction equation
c1ccc(N2CCCC2)cc1>B1Oc2ccccc2O1.CC(C)(O)C(C)(C)O.CCN(CC)CC.Cc1ccccc1.Fc1c(F)c(F)c(B(c2c(F)c(F)c(F)c(F)c2F)c2c(F)c(F)c(F)c(F)c2F)c(F)c1F>CC1(C)OB(c2ccc(N3CCCC3)cc2)OC1(C)C

Participants

7

Reactant 1

HCID 777261-Phenylpyrrolidine

Product 1

HCID 185257151-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrrolidineYield 92%

Reagents, catalysts & solvents 5

HCID 6425PinacolReagentHCID 8471TriethylamineReagentHCID 67506CatecholboraneReagentHCID 582056Tris(pentafluorophenyl)boraneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Prepared from 1-phenylpyrrolidine (1b, 29.4 mg, 0.200 mmol, 1.00 equiv) and catBH (36.0 mg, 0.300 mmol, 1.50 equiv) according to GP 1. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 3b (50.5 mg, 92%) as a white solid.

Sources & evidence

ORD record
ord-6d674ef84cd44a16a5f54277e04817b5
Source dataset
Borylation dataset from Roche

Reaction notes

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