(1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate → (1S,3R)-3-acetamido-2,2-dimethylcyclobutane-1-carboxylic acid

HRID 2179728ノート

反応式

HRID 2179728 の反応式
[C:1]([NH:4][C@@H:5]1[CH2:8][C@H:7]([C:9]([O:11]CC2C=CC=CC=2)=[O:10])[C:6]1([CH3:20])[CH3:19])(=[O:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([NH:4][C@@H:5]1[CH2:8][C@H:7]([C:9]([OH:11])=[O:10])[C:6]1([CH3:20])[CH3:19])(=[O:3])[CH3:2]

参加物

4

反応物 1

HCID 86650107(1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate

生成物 1

HCID 11183048(1S,3R)-3-acetamido-2,2-dimethylcyclobutane-1-carboxylic acid収率 54.9%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A stirred solution of (1S,3R)-benzyl 3-acetamido-2,2-dimethylcyclobutanecarboxylate (0.650 g, 2.36 mmol) in EtOAc (10 ml) at room temperature, 10% Pd/C (catalytic amount) were added and the reaction mixture was stirred under H2 gas atmosphere at room temperature for about 1 hour. After completion of the reaction (monitored by TLC), the reaction mixture was filtered through celite bed. The obtained filtrate was concentrated under reduced pressure to afford title compound as an off white solid. Wt: 0.240 g; Yield: 54.9%; 1H NMR (300 MHZ, CD3OD): δ 8.09 (d, J=3.0 Hz, 1H), 4.08-3.96 (m, 1H), 2.62-2.58 (m, 1H), 2.20-2.15 (m, 2H), 1.93 (s, 3H), 1.26 (s, 3H), 0.92 (s, 3H); Mass: [M+1]+ 186 (70%), [M+Na]+ 208 (93%). IR (KBr, cm−1): 3349, 2962, 1697, 1624, 1557, 1428, 1377, 1257, 1075, 988, 920, 736; M.R: 194.7° C.-216.2° C.

後処理

  1. customAfter completion of the reaction (monitored by TLC)
  2. filtrationthe reaction mixture was filtered through celite bed
  3. concentrationThe obtained filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-36ff39b084814270ae1bb442be98ed00
出典データセット
uspto-grants-2015_06
特許番号
US09067966B2

反応ノート

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