Ethyl acetate hexane → HCID 59371507, compound

HRID 2095361Notes

Reaction equation

HRID 2095361 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([C:20]#[C:21][C:22]2[CH:23]=[C:24]([CH2:28][OH:29])[CH:25]=[CH:26][CH:27]=2)[CH:17]=[N:18][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCOC(C)=O.CCCCCC>CCOC(C)=O.O=[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][C:22]2[CH:23]=[C:24]([CH2:28][OH:29])[CH:25]=[CH:26][CH:27]=2)[CH:17]=[N:18][CH:19]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 59371365HCID 59371365, compound

Product 1

HCID 59371507HCID 59371507, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a 50 mL round-bottom flask, a solution of 3-[[5-[[1-(tert-butoxycarbonyl)-(2S)-azetidinyl]methoxy]-3-pyridyl]ethynyl]phenylmethanol in EtOAc was hydrogenated over PtO2 with stirring at room temperature for 6.25 h. TLC (silica gel, EtOAc/hexane 3:1) showed a new spot (Rf 0.15) in place of the starting material (Rf 0.3), which was accompanied by a nonpolar impurity. The solution was concentrated and filtered over silica gel (11×1.3 cm, EtOAc). Evaporation of the product-containing fractions gave a quantitative yield of crude product, which by 1H NMR was shown to be a mixture of two major components in a molar ratio of approx. 4.5-5:1.

Workup

  1. concentrationThe solution was concentrated
  2. filtrationfiltered over silica gel (11×1.3 cm, EtOAc)
  3. customEvaporation of the product-containing fractions

Sources & evidence

ORD record
ord-3a3ae39a793b432d8fab1237d7eb38ec
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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