Acetic Acid → HCID 178484043、化合物

HRID 526225ノート

反応式

HRID 526225 の反応式
N[C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][CH2:3]1.C=O.[C:19]([BH3-])#[N:20].[Na+].[C:23](O)(=O)C>CO>[CH3:23][N:20]([CH3:19])[C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][CH2:3]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178453642HCID 178453642、化合物

生成物 1

HCID 178484043HCID 178484043、化合物収率 96%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of tert-butyl [trans-4-aminocyclohexyl]methylcarbamate (1.15 g, 5.00 mmol), paraformaldehyde (454 mg, 15.0 mmol), and sodium cyanoborohydride (940 mg, 15.0 mmol) in methanol (40 mL) was added acetic acid (catalytic) and the reaction mixture stirred at room temperature for 18 h. The reaction mixture was quenched with water and concentrated to remove methanol. The pH of the aqueous layer was adjusted to 10 with 1 M aqueous sodium hydroxide followed by extraction with methylene chloride. The organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to afford the desired product (1.2 g, 96%) as a thick oil: ESI MS m/z 257 [C14H28H2O2+H]+.

後処理

  1. customThe reaction mixture was quenched with water
  2. concentrationconcentrated
  3. customto remove methanol
  4. extractionfollowed by extraction with methylene chloride
  5. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-88ede687625e4d8fa03fe109dd9a356a
出典データセット
uspto-grants-2016_05
特許番号
US09345709B2

反応ノート

読み込み中…