3-Aminoazetidine, 3-BOC protected → tert-butyl N-[1-(2-methoxy-4-pyridinyl)azetidin-3-yl]carbamate

HRID 136

Reaction equation

HRID 136 reaction equation
CC(C)(C)OC(=O)NC1CNC1.COc1cc(Br)ccn1>CC(C)(C)[O-].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].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>COc1cc(N2CC(NC(=O)OC(C)(C)C)C2)ccn1

Participants

7

Reactant 2

HCID 15194053-Aminoazetidine, 3-BOC protectedHCID 140623094-Bromo-2-methoxypyridine

Product 1

HCID 118055029tert-butyl N-[1-(2-methoxy-4-pyridinyl)azetidin-3-yl]carbamateYield 100.28%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of all the reactants in toluene was heated in a sealed vial at 70 °C overnight. According to LC-MS the reaction was completed and the product had been formed. Toluene was removed, water was added and the product was extracted with DCM. The organic phase was dried through phase separator and concentrated. The crude was used without further purification in the next step, EN01762-02.

Sources & evidence

ORD record
ord-3870c5bc1f6548e38bd05a0e29b91f59
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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