Acetic Acid → (S)-1-(3-(Hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

HRID 528876노트

반응식

HRID 528876 반응식
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]([CH2:11][OH:12])[NH:2]1.[CH3:13][C:14](OC(C)=O)=[O:15].C([O-])([O-])=O.[K+].[K+].CC(O)=O>CCOC(C)=O.CO>[OH:12][CH2:11][C@@H:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1][N:2]1[C:14](=[O:15])[CH3:13]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 776757[(3S)-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol

생성물 1

HCID 86718900(S)-1-(3-(Hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone수율 72%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To (S)-(1,2,3,4-tetrahydroisoquinolin-3-yl)methanol (Aldrich, 350 mg, 2.14 mmol) in EtOAc (4.3 mL) and MeOH (1.1 mL) was added Ac2O (243 μL, 2.57 mmol). The resulting reaction mixture was stirred at room temperature for 2 h. K2CO3 was then added to neutralize the AcOH, and the reaction mixture was filtered through a pad of CELITE®, washing with EtOAc. The filtrate was concentrated in vacuo to give the title compound (316 mg, 72%) as a white solid. 1H NMR (CDCl3, 1.5:1 mixture of amide rotamers) δ 7.26-7.10 (m, 4H), 5.17 (d, J=18.0 Hz, 0.5H), 4.90 (dt, J=5.1, 9.4 Hz, 0.5H), 4.66-4.44 (m, 1H), 4.39-4.23 (m, 1H), 3.66-3.55 (m, 1H), 3.55-3.45 (m, 1H), 3.14 (dd, J=5.9, 16.3 Hz, 0.5H), 3.02 (dd, J=6.2, 15.8 Hz, 0.5H), 2.92-2.76 (m, 1H), 2.27 (s, 1H), 2.24 (s, 2H); MS(ESI+) m/z 206.1 (M+H)+.

후처리

  1. customThe resulting reaction mixture
  2. filtrationthe reaction mixture was filtered through a pad of CELITE®
  3. washwashing with EtOAc
  4. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-276bfa89e25b4663b75eedd530dd8eb1
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346795B2

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