tert-Butyl N-cyclopropylcarbamate → 1807546-55-9

HRID 1491049Notes

Reaction equation

HRID 1491049 reaction equation
CC(C)(C)OC(=O)NC1CC1>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]>CC(C)(C)OC(=O)NC1CC1B1OC(C)(C)C(C)(C)O1

Participants

6

Reactant 1

HCID 15698228tert-Butyl N-cyclopropylcarbamate

Product 1

HCID 1381119261807546-55-9Yield 2%

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

1f (200 mg, 1.3 mmol) and HBpin (0.28 mL, 1.9 mmol) were used. Purification was performed by MPLC (hexane/ethyl acetate = 10:1 to 3:1) to afford a mixture of 1f and 2f (NMR yield 2%). The mixture was purified again by MPLC (hexane/ethyl acetate = 6:1 to 3:2) to afford 2f as a white solid.

Sources & evidence

ORD record
ord-190a675c8ccc43a0837566a15ce408f6
Source dataset
Borylation dataset from Roche

Reaction notes

Loading…