HCID 70200856, compound → Isobutyl benzoate

HRID 1769832Notes

Reaction equation

HRID 1769832 reaction equation
C(OC(=O)C(C(O)=O)(CC)C(C[N+]([O-])=O)CC[C:9]1[CH:14]=[CH:13][C:12](CC(C)C)=[CH:11][C:10]=1[C:19]([OH:21])=[O:20])C>C(O)C.[Pt](=O)=O>[C:19]([O:21][CH2:9][CH:10]([CH3:19])[CH3:11])(=[O:20])[C:10]1[CH:9]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 70200856HCID 70200856, compound

Product 1

HCID 61048Isobutyl benzoate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 10.32 grams of 2-ethylcarboxy-3-nitromethyl-5-(4-(2,2-dimethylethyl)carboxyphenyl)pentanoic acid ethyl ester and 1.5 grams of platinum(IV) oxide in 200 ml of ethanol was hydrogenated in a Parr apparatus at an initial pressure of 50 psig H2. Filtration of the catalyst and removal of the solvent in vacuo provided the crude product as an oil which crystallized upon dissolution in 50 ml ether and addition of about 200 ml hexane until just cloudy. After stirring overnight, the crystalline material was filtered, washed with hexane, dried; affording 3.54 grams (42%) of 4-(2-oxo-3-carboethoxypyrrolidin-4-yl)ethyl)benzoic acid, 2,2-dimethylethyl ester. Selected data: mp 98°-104° C., 1H NMR (CDCl3) δ7.89 (d, J=8.2 Hz, 2H), 7.18 (d, J=8.2 Hz, 2H), 6.75 (s, 1H), 4.23 (q, 2H), 3.54 (dd, J=9.0, 8.3 Hz, 1H), 3.12 (d, J=8.6 Hz, 1H), 3.00 (dd, J=9.4, 7.4 Hz, 1H), 2.87 (m, 1H), 2.66 (t, J=7.6 Hz, 2H), 1.86 (m, 2H), 1.57 (s, 9H), 1.28 (t, 3H); 13C NMR (CDCl3) δ173.2, 169.7, 165.6, 145.8, 130.1, 129.7, 128.0, 80.8, 62.6, 54.4, 46.5, 38.9, 35.1, 32.4, 28.1, 14.1; MS(FAB) m/z 362 (7, M+ +1), 306 (100), 288 (22), Anal. Calcd for C20H27NO5 : C, 66.46; H, 7.53; N, 3.87. Found: C, 66.44; H, 7.77; N, 3.86.

Workup

  1. filtrationFiltration of the catalyst and removal of the solvent in vacuo
  2. customprovided the crude product as an oil which
  3. customcrystallized upon dissolution in 50 ml ether
  4. additionaddition of about 200 ml hexane until just cloudy
  5. filtrationthe crystalline material was filtered
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-1ea14bd823f3441bb461737a77a7ecc5
Source dataset
uspto-grants-1995_01
Patent number
US05382668

Reaction notes

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