Isobutyryl chloride → (3S)-1-Cbz-3-[cyclohexyl(isobutyryl)amino]pyrrolidine

HRID 1669999Notes

Reaction equation

HRID 1669999 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:23](Cl)(=[O:27])[CH:24]([CH3:26])[CH3:25]>C(Cl)Cl>[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([N:16]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 67343263HCID 67343263, compound

Product 1

HCID 67345617(3S)-1-Cbz-3-[cyclohexyl(isobutyryl)amino]pyrrolidineYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S)-1-Cbz-3-(cyclohexylamino)pyrolidine (4.75 g, 15.1 mmol) and TEA (4.26 mL, 30.2 mmol) in DCM (50 mL) was added dropwise isobutyryl chloride (1.15 mL, 60.3 mmol). The reaction mixture was stirred at rt for 12 h and quenched with 1N HCl solution. The organic material was extracted with DCM (50 mL×2) followed by EtOAc (50 mL×2), and the extracts were washed with a saline, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chomatography (EtOAc/Hex=1/3) to give the title compound (5.40 g, 96.7%).

Workup

  1. customquenched with 1N HCl solution
  2. extractionThe organic material was extracted with DCM (50 mL×2)
  3. washthe extracts were washed with a saline
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chomatography (EtOAc/Hex=1/3)

Sources & evidence

ORD record
ord-e207be9dbeb442b6affe3badd3719aae
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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