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4-Bromophenol → tert-butyl (3R)-4-(4-hydroxyphenyl)-3-methylpiperazine-1-carboxylate

HRID 664
Notes
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Reaction equation

HRID 664 reaction equation
C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1.Oc1ccc(Br)cc1>C1CCOC1.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)[O-].[K+].[Pd]>C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1ccc(O)cc1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 78084-BromophenolHCID 2756811(R)-1-Boc-3-methylpiperazine

Product 1

HCID 70873444tert-butyl (3R)-4-(4-hydroxyphenyl)-3-methylpiperazine-1-carboxylateYield 0%

Reagents, catalysts & solvents 4

HCID 23665647Potassium tert-butoxideReagentHCID 83681Tris(1,1-dimethylethyl)phosphineCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.025 g, 0.12 mmol), 4-bromophenol (0.043 g, 0.25 mmol), bis(tri-t- butylphosphine)palladium(0) (6.38 mg, 0.01 mmol) and [Reactants] in THF (2 mL) was flushed with nitrogen and sealed into a microwave tube. The reaction was heated to 100 °C for 20 minutes in the microwave reactor and cooled to RT. No trace of desired product by LCMS. The reaction was not progressed further.

Sources & evidence

ORD record
ord-512d2d9fb0454cb39e6db5113f92b34b
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes
HCID 2734558
Bis(tri-tert-butylphosphine)palladium(0)
Catalyst
HCID 8028TetrahydrofuranSolvent