9-Iodo-9-borabicyclo(3.3.1)nonane → 7-t-Butyl-5-[isopropyl-(4-hydroxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran

HRID 2290158Notes

Reaction equation

HRID 2290158 reaction equation
[C:1]([C:5]1[C:13]2[O:12][CH2:11][C:10]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([N:16]([CH:25]([CH3:27])[CH3:26])[C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=2)[C:6]=1[CH3:28])([CH3:4])([CH3:3])[CH3:2].IB1C2CCCC1CCC2>ClCCl.CCCCC>[C:1]([C:5]1[C:13]2[O:12][CH2:11][C:10]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([N:16]([CH:25]([CH3:26])[CH3:27])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:6]=1[CH3:28])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 5782319-Iodo-9-borabicyclo(3.3.1)nonaneHCID 186991847-t-Butyl-5-[isopropyl-(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran2×

Product 1

HCID 186991737-t-Butyl-5-[isopropyl-(4-hydroxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuranYield 131.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8003PentaneSolvent

Procedure

Following general procedure M and using 7-t-butyl-5-[isopropyl-(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran (Compound 57, 0.032 g, 0.083 mmol) and 1M solution of 9-iodo-9-borabicyclo[3.3.1]nonane (B-iodo-9-BBN) in hexanes (0.2 mL, 0.2 mmol) in 0.6 mL of anhydrous dichloromethane and 1 mL of n-pentane, the title compound (0.04 g) was obtained as a brown oil that was used in the next step without further purification.

Sources & evidence

ORD record
ord-34a4d56495b544debbb42daaf61dee4a
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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