1-Adamantanecarboxylic acid → Tricyclo(3.3.1.13,7)decane-1-carboxamide

HRID 1049292

反応式

HRID 1049292 の反応式
[C:1]12([C:11]([OH:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C1N=C[N:16](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-]>CCOC(C)=O>[C:1]12([C:11]([NH2:16])=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

参加物

5

反応物 3

HCID 132351-Adamantanecarboxylic acidHCID 14923Ammonium HydroxideHCID 682631,1'-Carbonyldiimidazole

生成物 1

HCID 21686Tricyclo(3.3.1.13,7)decane-1-carboxamide収率 87.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A solution of adamantane-1-carboxylic acid (2.00 g, 11.10 mmol) in EtOAc (20 mL) was treated with CDI (2.00 g, 12.33 mmol), stirred at RT for 20 minutes, treated with NH4OH (˜14M, 5 mL, ˜70 mmol) and stirred at RT for 20 minutes. The mixture was concentrated to dryness, treated with satd. NaHCO3 and the solids collected via filtration and dried to afford adamantane-1-carboxamide (1.74 g, 87%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.91 (s, 1H), 6.65 (s, 1H), 1.92 (m, 3H), 1.74-1.71 (m, 6H), 1.68-1.57 (m, 6H); MS (ESI) m/z: 180.1 (M+H+).

後処理

  1. stirringstirred at RT for 20 minutes
  2. concentrationThe mixture was concentrated to dryness
  3. additiontreated with satd
  4. filtrationNaHCO3 and the solids collected via filtration
  5. customdried

出典と根拠

ORDレコード
ord-c055df6e0f4f403b8cba3642423ddf68
出典データセット
uspto-grants-2016_07
特許番号
US09382228B2

関連ノート

読み込み中…