HCID 103713505, compound → HCID 178439604, compound

HRID 1491050Notes

Reaction equation

HRID 1491050 reaction equation
CCCC1CC1NC(=O)C(C)(C)C>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCCCC1.CC1(C)OBOC1(C)C.C[OH2+].C[OH2+].Cc1cnc2c(ccc3c(C)c(C)cnc32)c1C.[Ir].[Ir]>CCCC1C(NC(=O)C(C)(C)C)C1B1OC(C)(C)C(C)(C)O1

Participants

6

Reactant 1

HCID 103713505HCID 103713505, compound

Product 1

HCID 178439604HCID 178439604, compoundYield 23%

Reagents, catalysts & solvents 4

HCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8078CyclohexaneSolvent

Conditions

Temperature
80 °C

Procedure

1j (15.0 mg, 81 µmol) and HBpin (17.8 µL, 0.12 mmol) were used. Purification was performed by MPLC (hexane/ethyl acetate = 9:1 to 7:3, then hexane/ether = 1:1 to 0:1), and finally by GPC to afford 5.9 mg of 2j as a colorless oil in a 23% yield. NOE was observed between H-1 and H-3 and not observed between H-1 and H-2. This result indicates that 2j has cis configuration between the N group and the B group

Sources & evidence

ORD record
ord-84a1619a2aaa485aa3d6761aec50cd2f
Source dataset
Borylation dataset from Roche

Reaction notes

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