Trimethylphosphine → (2S,4S)-1-Boc-4-amino-2-[(4-methylpiperazin-1-yl)carbonyl]pyrrolidine

HRID 1927564Notes

Reaction equation

HRID 1927564 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+]=[N-])[CH2:10][C@H:9]1[C:16]([N:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1)=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CP(C)C>C1COCC1>[C:1]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@H:9]1[C:16]([N:18]1[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]1)=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 68983TrimethylphosphineHCID 86641588(2S,4S)-1-Boc-4-azido-2-[(4-methylpiperazin-1-yl)carbonyl]pyrrolidine

Product 1

HCID 67358152(2S,4S)-1-Boc-4-amino-2-[(4-methylpiperazin-1-yl)carbonyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S,4S)-1-Boc-4-azido-2-[(4-methylpiperazin-1-yl)carbonyl]pyrrolidine (11.67 g, 34.48 mmol) obtained in Step B was dissolved in THF (30 mL). Trimethyl phosphine (3.40 mL, 38.37 mmol) was added dropwise thereto at 0-5° C. The reaction solution was stirred for 2 hours at room temperature, concentrated in vacuo and basified with saturated NaHCO3 aqueous solution. The solution was extracted with EtOAc two times and concentrated in vacuo to give the title compound in oil form (10.61 g, 98.5%).

Workup

  1. customat 0-5° C
  2. concentrationconcentrated in vacuo
  3. extractionThe solution was extracted with EtOAc two times
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70c639202b434d74a143fbe04d1e5e99
Source dataset
uspto-grants-2012_05
Patent number
US08183243B2

Reaction notes

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