Ethyl Acetate → (S)-tert-butyl 2-(4-(4-bromophenyl)hydroxy-5-propyl-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 80396노트

반응식

HRID 80396 반응식
[OH-].[NH4+:2].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)/[C:11](=[N:15]\[OH:16])/[CH2:12][CH2:13][CH3:14])=[CH:6][CH:5]=1.[C:18]([N:25]1[CH2:31][CH2:30][CH2:29][C@H:26]1[CH:27]=O)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(OCC)(=O)C>CO>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:2]=[C:27]([C@@H:26]3[CH2:29][CH2:30][CH2:31][N:25]3[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:15]([OH:16])[C:11]=2[CH2:12][CH2:13][CH3:14])=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 87519930(2Z)-1-(4-bromophenyl)-2-hydroxyiminopentan-1-one

생성물 1

HCID 57610963(S)-tert-butyl 2-(4-(4-bromophenyl)hydroxy-5-propyl-1H-imidazol-2-yl)pyrrolidine-1-carboxylate수율 34.5%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
24 °C

실험 절차

The 28% ammonium hydroxide (15 mL) was added to a solution of (Z)-1-(4-bromophenyl)-2-(hydroxyimino)pentan-1-one (1.5 g, 5.55 mmol) and (S)—N—BOC-prolinal (1.1 g, 5.55 mmol) in methanol (60 mL) and stirred for 18 hours at 24° C. The reaction mixture was partitioned between CH2Cl2 and water and the organic phase concentrated and applied (CH2Cl2) to a 40 (M) Biotage silica gel column. Gradient elution, 5-100%, over 1L (A=Hexanes; B=ethyl acetate) gave (S)-tert-butyl 2-(4-(4-bromophenyl)hydroxy-5-propyl-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (863 mg, 34.5% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.54 (m, 4H), 5.0-4.88 (m, 1H), 3.53-3.41 (m, 1H), 3.41-3.36 (m, 1H), 2.72 (t, J=7.0 Hz, 2H), 2.24-2.03 (m, 2H), 1.96-1.91 (m, 1H), 1.89-1.81 (m, 1H), 1.60 (h, J=7.6 Hz, 2H), 1.39/1.17 (s, 9H). 0.92 (t, J=7.0 Hz, 3H). RT=1.9 min, (Condition 1) LCMS: Anal. Calcd. for C21H28BrN3O3 450.13; found: 450.33 (M+H)+.

후처리

  1. customThe reaction mixture was partitioned between CH2Cl2 and water
  2. concentrationthe organic phase concentrated
  3. washGradient elution, 5-100%

출처 및 근거

ORD 기록
ord-0409839569d64e3189af2c2850a37705
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846023B2

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