Methylamine → HCID 56614350, compound

HRID 2371389Notes

Reaction equation

HRID 2371389 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C@H:17]([OH:19])[CH2:16][C@H:12]1[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([N:22](CC)CC)C.ClC(OCC)=O.CN>ClCCl.CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C@H:17]([OH:19])[CH2:16][C@H:12]1[C:13]([NH:22][CH3:20])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Product 1

HCID 56614350HCID 56614350, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

trans-1-Benzyloxycarbonyl-4-hydroxy-L-proline (3.06 g) was dissolved in dry dichloromethane (48 ml), and triethylamine (1.75 ml) was added thereto, followed by addition of ethyl chloroformate (1.88 g) at -50° C. under nitrogen stream. The resultant mixture was stirred at -30° to -50° C. for 30 minutes, and a solution of methylamine (1.44 g) in dichloromethane (5 ml) and methanol (3.7 ml) was added thereto at -50° C. Stirring was continued at -30° to -50° C. for 20 minutes. The reaction mixture was successively washed with dilute hydrochloric acid, aqueous sodium chloride solution, dilute sodium hydroxide solution and sodium chloride solution and dried over magnesium sulfate. After removal of the solvent, the residue was crystallized from ether to give (2S,4R)-1-benzyloxycarbonyl-2-methylaminocarbonyl-4-hydroxypyrrolidine.

Workup

  1. customat -50° C
  2. washThe reaction mixture was successively washed with dilute hydrochloric acid, aqueous sodium chloride solution, dilute sodium hydroxide solution and sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-a1b729bcb24d42d59d0d4d6ad330d8f1
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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