Dimethylformamide → Tert-butyl 3-aminoazetidine-1-carboxylate

HRID 598810Notes

Reaction equation

HRID 598810 reaction equation
[CH:1]([NH2:14])(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:15]([Mg]Br)[CH:16]=[CH2:17].B1C2CCC[CH:21]1CCC2.[C:29]([O-:32])(O)=[O:30].[Na+].C([O-])([O-])=O.[K+].[K+].[CH3:40][N:41]([CH:43]=O)C>[OH-].[OH-].[Pd+2].[Pd].CO.C(Cl)Cl.CCN(CC)CC.CCO>[C:16]([O:32][C:29]([N:41]1[CH2:43][CH:1]([NH2:14])[CH2:40]1)=[O:30])([CH3:17])([CH3:21])[CH3:15]

Participants

13

Reactant 6

HCID 6228DimethylformamideHCID 7036BenzhydrylamineHCID 11430Potassium Carbonate2×HCID 789669-Borabicyclo(3.3.1)nonaneHCID 516892Sodium BicarbonateHCID 178455850HCID 178455850, compound

Product 1

HCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylate

Reagents, catalysts & solvents 6

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Key: (a) benzhydrylamine, MeOH, 72 hours, 23° C., then reflux 72 hours; (b) MeOH, EtOH (1:1), Pd(OH)2 (20%), 12 hours; (c) Boc2, sat. NaHCO3, 24 hours; (d) MsCl, Et3N, CH2Cl2, 1 hour, 83%; (e) NaN3, DMF, 70° C., 72 hours, then H2, Pd—C (10%), MeOH, 5-6 hours, quantitative.

Sources & evidence

ORD record
ord-6aa2b81af9c1421fa67cf90d6a3b0f56
Source dataset
uspto-grants-2011_03
Patent number
US07897635B2

Reaction notes

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