HCID 57446165, compound → HCID 57446166, compound

HRID 1172395Notes

Reaction equation

HRID 1172395 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]([C:12](=O)[CH2:13][CH2:14][C:15]#[N:16])([CH3:11])[CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[CH3:2]>C(O)(=O)C.Cl.[Pt]=O>[CH2:1]([O:3][C:4](=[O:18])[C:5]([CH3:11])([CH:12]1[CH2:13][CH2:14][CH2:15][NH:16]1)[CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2]

Participants

5

Reactant 1

HCID 57446165HCID 57446165, compound

Product 1

HCID 57446166HCID 57446166, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2-(3-cyano-propionyl)-2,5-dimethyl-hex-4-enoic acid ethyl ester (323 mg, 1.29 mmol) in acetic acid (20 mL) was treated with one drop of 18.0 M aqueous hydrochloric acid solution and platinum oxide (29 mg, 0.129 mmol). The reaction mixture was degassed and hydrogenated under 50 psi of hydrogen gas for 12 h. The reaction mixture was filtered over celite and the filtrate was concentrated in vacuo. The residue was treated with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford the desired product, 2,5-dimethyl-2-pyrrolidin-2-yl-hexanoic acid ethyl ester (271 mg, 87%) as a light brown oil. This material was directly used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ: 0.87-0.89 (6H, m), 0.97-1.07 (1H, m), 1.13 (3H, s), 1.15-1.22 (1H, m), 1.24-1.29 (3H, m), 1.38-1.57 (3H, m), 1.67-1.81 (4H, m), 2.86-3.00 (2H, m), 3.28-3.36 (1H, m), 4.11-4.18 (2H, m). LC-MS (ESI) calcd for C14H27NO2: 241.20, found 242.4 [M+H+].

Workup

  1. customThe reaction mixture was degassed and hydrogenated under 50 psi of hydrogen gas for 12 h
  2. filtrationThe reaction mixture was filtered over celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was treated with saturated aqueous sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db01ba7f7f954f20b84c13a1cbe86429
Source dataset
uspto-grants-2010_11
Patent number
US07834009B2

Reaction notes

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