p-Toluenesulfonic acid → Tert-butyl 3-aminoazetidine-1-carboxylate

HRID 1372189Notes

Reaction equation

HRID 1372189 reaction equation
[CH:1]([NH2:14])([C:8]1[CH:13]=CC=CC=1)C1C=CC=CC=1.C([Mg]Br)C=C.[CH3:20][C:21]([O:24][C:25]([O:27]C(OC(C)(C)C)=O)=O)([CH3:23])[CH3:22].C([O-])(O)=O.[Na+].C([O-])([O-])=O.[K+].[K+].CC1C=CC(S(O)(=O)=O)=CC=1.C[N:58](C=O)C>[OH-].[OH-].[Pd+2].[Pd].CO.C(Cl)Cl.CCN(CC)CC.CCO>[C:21]([O:24][C:25]([N:14]1[CH2:1][CH:8]([NH2:58])[CH2:13]1)=[O:27])([CH3:23])([CH3:22])[CH3:20]

Participants

14

Reactant 7

HCID 6101p-Toluenesulfonic acidHCID 6228DimethylformamideHCID 7036BenzhydrylamineHCID 11430Potassium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 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) Boc2O, 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-b77e7b11b1d2444cafd2756be43a0a71
Source dataset
uspto-grants-2007_01
Patent number
US07157489B2

Reaction notes

Loading…