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

HRID 137

Reaction equation

HRID 137 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 99.96%

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.

Sources & evidence

ORD record
ord-f3ebf4dfde174cff92751e3b49ce74da
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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