1-Bromo-4-phenylmethoxybenzene → (R)-4-(4-benzyloxyphenyl)-3-methylpiperazine-1-carboxylic acid tert-butyl ester

HRID 109

Reaction equation

HRID 109 reaction equation
Brc1ccc(OCc2ccccc2)cc1.C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1>CC(C)(C)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd]>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(OCc2ccccc2)cc1

Participants

7

Reactant 2

HCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 2756811(R)-1-Boc-3-methylpiperazine

Product 1

HCID 70873375(R)-4-(4-benzyloxyphenyl)-3-methylpiperazine-1-carboxylic acid tert-butyl esterYield 0%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.072 g, 0.36 mmol), 1-(benzyloxy)-4-bromobenzene (0.079 g, 0.3 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.035 g, 0.06 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.027 g, 0.03 mmol) and sodium 2-methylpropan-2-olate (0.101 g, 1.05 mmol) in toluene (2 mL) was flushed with nitrogen and sealed into a microwave tube. The reaction was heated to 150 °C for 10 minutes in the microwave reactor and cooled to RT. Only a small amount of the desired product was visible by LCMS. The reaction was not progressed further.

Sources & evidence

ORD record
ord-8d2093b827454e2d9150258e88282b25
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

Loading…