1-(2-Pyridyl)piperazine → HCID 58487957, compound

HRID 1677778Notes

Reaction equation

HRID 1677778 reaction equation
[CH3:1][C:2]1([CH3:27])[O:6][C@@H:5]([C@H:7]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:8]([O:10]C2C(F)=C(F)C(F)=C(F)C=2F)=O)[C:4](=[O:26])[O:3]1.ONC(=O)[C@@H](O)[C@@H](C([N:39]1[CH2:44][CH2:43][N:42]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=2)[CH2:41][CH2:40]1)=O)CC(C)C.N1C=CC=CC=1N1CCNCC1>CN(C=O)C>[CH3:27][C:2]1([CH3:1])[O:3][C:4](=[O:26])[C@H:5]([C@@H:7]([C:8]([N:39]2[CH2:44][CH2:43][N:42]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=3)[CH2:41][CH2:40]2)=[O:10])[CH2:22][CH:23]([CH3:24])[CH3:25])[O:6]1

Participants

5

Reactant 3

HCID 944591-(2-Pyridyl)piperazineHCID 11653205HCID 11653205, compound2×HCID 86617975HCID 86617975, compound

Product 1

HCID 58487957HCID 58487957, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of a 55/45 diastereoisomeric mixture of pentafluorophenyl (2S)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoate and pentafluorophenyl (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoate (Intermediate 1, 792.6 mg; 2.0 mmol; 1.0 eq.) in DMF (15 mL) was added 1-(2-pyridyl)piperazine (326.5 mg; 2.0 mmol; 1.0 eq.). After 14 h of reaction at RT, the solvent was evaporated to give an oil. Purification by chromatography (SiO2) gave the title compound as a colorless oil (as a mixture of 2 diastereoisomers 50/50). This product was dissolved on iPrOH (10 mL) at kept at −20° C. for 48 h. The supernatant was collected and evaporated to give a colorless oil (301 mg, 40%, single diastereoisomer). M+(ESI): 376.3. HPLC (Condition A): Rt: 5.0 min (HPLC purity: 77.1%). 1H NMR (CDCl3, 300 MHz) δ 8.22 (d, J=4.2 Hz, 1H), 7.58-7.47 (m, 1H), 6.74-6.63 (m, 2H), 4.54 (d, J=6.0 Hz, 1H), 3.88-3.41 (m, 8H), 3.33-3.22 (m, 1H), 1.89-1.62 (m, 3H), 1.61 (s, 3H), 1.55 (s, 3H), 0.99-0.88 (m, 6H).

Workup

  1. customAfter 14 h of reaction at RT
  2. customthe solvent was evaporated
  3. customto give an oil
  4. customPurification by chromatography (SiO2)

Sources & evidence

ORD record
ord-8686690393564ea4a078c0bcc952a9ce
Source dataset
uspto-grants-2011_08
Patent number
US08008302B2

Reaction notes

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