Morpholine → HCID 58092702, compound

HRID 2066794Notes

Reaction equation

HRID 2066794 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[C@H:9]([CH2:10]I)[CH2:8][CH2:7][N:6]1[C@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])=[O:4].C([O-])([O-])=O.[K+].[K+].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(#N)C>[CH3:1][O:2][C:3]([C@@H:5]1[C@H:9]([CH2:10][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH2:8][CH2:7][N:6]1[C@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])=[O:4]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 58092804HCID 58092804, compound

Product 1

HCID 58092702HCID 58092702, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (2S,3R)-3-iodomethyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid methyl ester (Step 5.5) (7.07 mmol), K2CO3 (21.22 mmol) and morpholine (10.61 mmol) in acetonitrile (24 mL) was stirred at 50° C. for 62 h. The reaction mixture was poured onto ice water and extracted with EtOAc (3×). The combined organic layers were successively washed with water and brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a yellow oil. HPLC: tR=2.56 min (method A); ESI-MS: [M+H]+ 333.

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were successively washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-b5da541f46624b2997908bed8cbd67b9
Source dataset
uspto-grants-2012_10
Patent number
US08293753B2

Reaction notes

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