(3R)-3-Phenylpyrrolidine--hydrogen chloride (1/1) → HCID 57513844, compound

HRID 2368441Notes

Reaction equation

HRID 2368441 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]([CH3:19])([NH:6][C:7](OC1C=CC([N+]([O-])=O)=CC=1)=[O:8])[CH3:5].Cl.[C:22]1([C@H:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[C:4]([CH3:19])([NH:6][C:7]([N:30]1[CH2:31][CH2:32][C@H:28]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:29]1)=[O:8])[CH3:5]

Participants

5

Reactant 2

HCID 44891082(3R)-3-Phenylpyrrolidine--hydrogen chloride (1/1)HCID 57476907HCID 57476907, compound

Product 1

HCID 57513844HCID 57513844, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Combine 2-methyl-2-(4-nitro-phenoxycarbonylamino)-propionic acid methyl ester (500 mg, 1.77 mmol) and (R)-3-phenyl-pyrrolidine hydrochloride (325 mg, 1.77 mmol) in 1,4-dioxane (5 mL). Add TEA (494 uL, 3.54 mmol) and heat to 130° C. for 5 min by microwave irradiation. Dilute the reaction mixture with DCM (100 mL) and extract with 1 N NaOH (30 mL) followed by 1 N HCl (30 mL). Dry the organic layer over MgSO4 and concentrate. Purify the concentrate by silica gel chromatography (40-60% EtOAc/HEP) to afford the title compound: 1H NMR (400 MHz, DICHLOROMETHANE-d2) 1.51 (d, J=1.77 Hz, 6H) 1.98-2.14 (m, 1H) 2.22-2.38 (m, 1H) 3.31 (t, J=9.28 Hz, 1H) 3.35-3.48 (m, 2H) 3.53-3.65 (m, 1H) 3.70 (s, 3H) 3.80 (dd, J=9.41, 7.52 Hz, 1H) 7.15-7.40 (m, 5H).

Workup

  1. extractionextract with 1 N NaOH (30 mL)
  2. dry with materialDry the organic layer over MgSO4
  3. concentrationconcentrate
  4. customPurify the
  5. concentrationconcentrate by silica gel chromatography (40-60% EtOAc/HEP)

Sources & evidence

ORD record
ord-0a874a852020474b9cd2a55fde7e8170
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

Loading…