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

HRID 2404494Notes

Reaction equation

HRID 2404494 reaction equation
[CH3:1][NH2:2].[CH:3]12[O:8][CH:7]1[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]2>C(OC(C)C)(C)C>[OH:8][CH:3]1[CH:7]([NH:2][CH3:1])[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 21736783Tert-butyl 3-hydroxy-4-(methylamino)pyrrolidine-1-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

Aqueous methylamine solution (40% solution, 812 mL, 3.8 mol) was added to the epoxide 3 (140 g, 0.65 mol) at room temperature and the reaction was stirred until complete. The excess methylamine was removed by distillation under reduced pressure. To the residue obtained, diisopropyl ether (800 mL) was added and the mixture stirred for about 30 min. The solid was filtered, washed with diisopropyl ether (200 mL), then dried to give compound 4 (135 g).

Workup

  1. customThe excess methylamine was removed by distillation under reduced pressure
  2. customTo the residue obtained
  3. stirringthe mixture stirred for about 30 min
  4. filtrationThe solid was filtered
  5. washwashed with diisopropyl ether (200 mL)
  6. customdried

Sources & evidence

ORD record
ord-c912b3b67c224d90bafc4feab7a4f761
Source dataset
uspto-grants-2014_08
Patent number
US08802719B2

Reaction notes

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