Dimethylamine, hydrochloride → HCID 15117320, compound

HRID 1029674Notes

Reaction equation

HRID 1029674 reaction equation
[C:1]([CH:4]1[CH2:8][N:7]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[C@H:6]([C:15]([OH:17])=O)[CH2:5]1)(=[O:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:30][NH:31][CH3:32].C(N=C=NCCCN(C)C)C>O1CCCC1.O.C(OCC)(=O)C>[C:1]([CH:4]1[CH2:8][N:7]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[C@H:6]([C:15](=[O:17])[N:31]([CH3:32])[CH3:30])[CH2:5]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 15117319HCID 15117319, compound

Product 1

HCID 15117320HCID 15117320, compoundYield 42.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S)-4-acetyl-1-allyloxycarbonylpyrrolidine-2-carboxylic acid (23.27 g) in tetrahydrofuran (230 ml) were added in turn 1-hydroxybenzotriazole hydrate (13.7 g), dimethylamine hydrochloride (8.27 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (18.5 ml) at 0° C. After 2 hours, the reaction mixture was poured into a mixture of ethyl acetate and water, the organic layer was separated, washed twice with saturated aqueous layer hydrogen carbonate and brine in turn. The solvent was dried over magnesium sulfate and removed in vacuo. The residue was chromatographed on silica gel (600 ml) eluting with a mixture of dichloromethane and acetone (6:1→4:1) to give (2S)-4-acetyl-1-allyloxycarbonyl-2-dimethylcarbamoylpyrrolidine (11 g).

Workup

  1. customthe organic layer was separated
  2. washwashed twice with saturated aqueous layer hydrogen carbonate and brine in turn
  3. dry with materialThe solvent was dried over magnesium sulfate
  4. customremoved in vacuo
  5. customThe residue was chromatographed on silica gel (600 ml)
  6. washeluting with a mixture of dichloromethane and acetone (6:1→4:1)

Sources & evidence

ORD record
ord-5777b9e301d54c36acf4cec89613a4a5
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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