Pyridine → HCID 67256139, compound

HRID 1821746Notes

Reaction equation

HRID 1821746 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6](Cl)=[O:7].[CH2:15]([N:22]1[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH2:15]([N:22]1[CH2:26][CH2:25][C@H:24]([O:27][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinolHCID 111276553-methoxy-4-nitro-benzoyl Chloride

Product 1

HCID 67256139HCID 67256139, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 3-methoxy-4-nitro-benzoyl chloride (608 mg, 2.82 mmol) in 10 mL of CH2Cl2 was added to stirred solution of 500 mg (2.82 mmol) of (3S)-1-benzyl-pyrrolidin-3-ol and 1 mL of pyridine in 15 mL CH2Cl2 at room temperature. After stirring for 18 h, the reaction mixture was diluted with 20 mL of saturated aqueous NaHCO3 and extracted with CH2Cl2 (2×10 mL). The combined extracts were washed with 20 mL of brine, dried over MgSO4, filtered, and concentrated in vacuo to furnish 780 mg (71%) of the desired ester as a yellow oil, which solidified after drying under high vacuum. The resulting solid was further purified by trituration with 1:1 ether-hexane. 1H-NMR (400 MHz, CDCl3) δ 7.83 (d, J=7.83 Hz, 1H), 7.74 (s, 1H), 7.68 (d, J=7.83 Hz, 1H), 7.2-7.4 (m, 5H), 5.44 (br.m, 1H), 4.02 (s, 2H), 3.69 (dd, J=30 Hz, J=13 Hz, 1H), 2.8-3.0 (m, 2H), 2.5-2.6 (m, 1H), 2.3-2.45 (m, 1H); 2.0-2.1 (m, 1H).

Workup

  1. extractionextracted with CH2Cl2 (2×10 mL)
  2. washThe combined extracts were washed with 20 mL of brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a3fbd96f9564c8fb4149e56b4e12fe6
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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