Nitrogen → 3-(3-Oxocyclobutyl)propanoic acid

HRID 707671

反応式

HRID 707671 の反応式
C([O:8][C:9](=[O:17])[CH2:10][CH2:11][CH:12]1[CH2:15][C:14](=[O:16])[CH2:13]1)C1C=CC=CC=1.N#N>C(OCC)(=O)C.[Pd]>[O:16]=[C:14]1[CH2:15][CH:12]([CH2:11][CH2:10][C:9]([OH:17])=[O:8])[CH2:13]1

参加物

5

反応物 2

HCID 947NitrogenHCID 67774851Benzyl 3-(3-oxocyclobutyl)propanoate

生成物 1

HCID 677753573-(3-Oxocyclobutyl)propanoic acid収率 99.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 3-(3-Oxo-cyclobutyl)-propionic acid benzyl ester (9) (8.12 g, 34.96 mmol) in ethyl acetate (80 ml) was purged 3× with N2 before 10% Pd/C (800 mg, 0.077 mmol, ˜2 mol %) was added. The reaction mixture was purged again 3× with N2 then twice with H2 before leaving the reaction under an atmosphere of H2. The reaction was monitored by LCMS until no more sign of starting material was observed (˜10 h). The reaction was purged with 3 times N2, filtered through celite and Pd/C was washed 3× with ˜25 ml of EtOAc. The combined organic were concentrated to yield 4.94 g (99%) of 10 as a light yellow oil. NMR analysis shows clean product, no further purification was required. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 11.46 (1 H, br. s.), 3.09-3.29 (2 H, m), 2.63-2.80 (2 H, m), 2.35-2.53 (3 H, m), 1.95 (2 H, q, J=7.57 Hz).

後処理

  1. additionwas added
  2. customThe reaction mixture was purged again 3× with N2
  3. customtwice with H2 before leaving
  4. customthe reaction under an atmosphere of H2
  5. custom(˜10 h)
  6. customThe reaction was purged with 3 times N2
  7. filtrationfiltered through celite and Pd/C
  8. washwas washed 3× with ˜25 ml of EtOAc
  9. concentrationThe combined organic were concentrated

出典と根拠

ORDレコード
ord-95ff79cbd14f47ca952b2a1cee5c4b3f
出典データセット
uspto-grants-2015_11
特許番号
US09175032B2

関連ノート

読み込み中…