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

HRID 520355노트

반응식

HRID 520355 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-3c7d8aaeb009425fae92efd3b5df1c62
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326973B2

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