N-Benzoylbenzylamine → N-benzyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 1491069Notes

Reaction equation

HRID 1491069 reaction equation
O=C(NCc1ccccc1)c1ccccc1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1[nH]c2c(NC(=O)c3ccc(-c4ccccn4)nc3)cccc2c1C.[Ir].[Ir]>CC1(C)OB(c2ccccc2C(=O)NCc2ccccc2)OC1(C)C

Participants

6

Reactant 1

HCID 73878N-Benzoylbenzylamine

Product 1

HCID 172840361N-benzyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideYield 65%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 178433626HCID 178433626, compoundReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Isolated by chromatography using deactivated silica gel and ethyl acetate and petroleum ether (10:1 to 1:1) as the eluent.

Sources & evidence

ORD record
ord-595736498a9142558380004d6497216a
Source dataset
Borylation dataset from Roche

Reaction notes

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