2,6-Lutidine → (S)-4-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)benzonitrile

HRID 1948495노트

반응식

HRID 1948495 반응식
[Br:1][CH2:2][C@H:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)[OH:4].CC1C=CC=C(C)N=1.[Si:21](OS(C(F)(F)F)(=O)=O)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(Cl)Cl.C(OCC)(=O)C>[Br:1][CH2:2][C@H:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)[O:4][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

참가 물질

6

반응물 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 66955119(S)-4-(2-bromo-1-hydroxyethyl)benzonitrile

생성물 1

HCID 66955431(S)-4-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)benzonitrile수율 115.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of (S)-4-(2-bromo-1-hydroxyethyl)benzonitrile (6.9 g, 30.5 mmol) and 2,6-dimethylpyridine (7.82 mL, 67.1 mmol) in DCM (20 mL) was added t-butyl-dimethylsilyltrifluoromethanesulfonate (14.02 mL, 61.0 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried MgSO4, filtered and concentrated. The crude material was purified on a 80 gram silica column and eluting with an EtOAc/Hex gradient to afford 12 g of (S)-4-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)benzonitrile. MS (M+1)=340/342. HPLC Peak RT=2.16 minutes. 1H NMR (400 MHz, CDCl3) δ ppm 7.65 (2H, d), 7.45 (2H, d), 4.88 (1H, dd), 3.42 (1H, q), 3.39 (1H, dd), 0.85 (9H, s), 0.12 (3H, s), −0.09 (3H, s).

후처리

  1. washwashed with saturated NaCl
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude material was purified on a 80 gram silica column
  5. washeluting with an EtOAc/Hex gradient

출처 및 근거

ORD 기록
ord-8abf08f4b5074a09b24362d3ebe14aa7
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399451B2

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