Acetonitrile → Tert-butyl 3-hydroxy-4-(methylamino)pyrrolidine-1-carboxylate

HRID 455002

Reaction equation

HRID 455002 reaction equation
[C:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].BrN1C(C)(C)C(=O)N(Br)C1=[O:16].[C:24](#[N:26])C>>[OH:16][CH:11]1[CH:10]([NH:26][CH3:24])[CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:12]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 5148195tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 21736783Tert-butyl 3-hydroxy-4-(methylamino)pyrrolidine-1-carboxylate

Procedure

N-Boc-3-pyrroline (1) (16 kg) was treated with 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) (15.2 kg) in aqueous ACN to form the bromohydrin (2). After the reaction was complete, the excess brominating agent was quenched with aqueous sodium thiosulfate solution and the crude reaction mixture was treated with aqueous NaOH. The resulting epoxide was extracted with MTBE and the organic layer was concentrated to give the crude epoxide (3). This epoxide was added to 40% aqueous methylamine and, after the reaction was complete, the excess methylamine and water were removed by distillation and the product, (4), (18.5 kg) was isolated from diisopropyl ether.

Sources & evidence

ORD record
ord-549df69d72d144ea8860d72d6bdf7831
Source dataset
uspto-grants-2013_07
Patent number
US08497282B2

Linked notes

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