Trimethylsilyl cyanide → (S)-2-((R)-2-hydroxy-1-phenylethylamino)-2-(1-methylcyclopropyl)acetonitrile

HRID 520355ノート

反応式

HRID 520355 の反応式
[CH3:1][C:2]1([CH:5]=O)[CH2:4][CH2:3]1.[NH2:7][C@H:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][OH:10].C[Si]([C:21]#[N:22])(C)C>CO>[OH:10][CH2:9][C@H:8]([NH:7][C@@H:5]([C:2]1([CH3:1])[CH2:3][CH2:4]1)[C:21]#[N:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 82115Trimethylsilyl cyanideHCID 2724025(R)-beta-aminophenethyl alcoholHCID 101976191-Methylcyclopropane-1-carbaldehyde

生成物 1

HCID 86690076(S)-2-((R)-2-hydroxy-1-phenylethylamino)-2-(1-methylcyclopropyl)acetonitrile

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 1-methylcyclopropanecarbaldehyde in MeOH (20 mL) was added (R)-2-amino-2-phenylethanol (3.23 g, 23.54 mmol) at rt under N2 in 3 portions. The mixture was stirred at rt for 2 h and then cooled down with ice-water bath and added with trimethylsilyl cyanide (5.74 mL, 42.8 mmol) dropwise over 5 min. The mixture was stirred for 10 min, ice bath was removed and the reaction was stirred at rt overnight. The reaction mixture was concentrated and purified on a 40 g silica gel column (EtOAc/hexane: 0 to 100%) to afford (S)-2-((R)-2-hydroxy-1-phenylethylamino)-2-(1-methylcyclopropyl)acetonitrile. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.40-7.30 (m, 5H), 4.08 (dd, J=9.2, 4.1 Hz, 1H), 3.82 (dd, J=10.8, 4.0 Hz, 1H), 3.64 (t, J=10.0 Hz, 1H), 2.97 (s, 1H), 1.26 (s, 3H), 0.63-0.53 (m, 2H), 0.51-0.42 (m, 2H).

後処理

  1. temperaturecooled down with ice-water bath
  2. stirringThe mixture was stirred for 10 min
  3. customice bath was removed
  4. stirringthe reaction was stirred at rt overnight
  5. concentrationThe reaction mixture was concentrated
  6. custompurified on a 40 g silica gel column (EtOAc/hexane: 0 to 100%)

出典と根拠

ORDレコード
ord-3c7d8aaeb009425fae92efd3b5df1c62
出典データセット
uspto-grants-2016_05
特許番号
US09326973B2

反応ノート

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