Triphenylphosphine → tert-butyl-3-(3-methyl-4-nitro-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate

HRID 928199노트

반응식

HRID 928199 반응식
[CH3:1][C:2]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][NH:4][N:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH:19](O)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:21][CH2:20][CH:19]([N:4]2[CH:5]=[C:6]([N+:7]([O-:9])=[O:8])[C:2]([CH3:1])=[N:3]2)[CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 44169391-Boc-3-pyrrolidinolHCID 178434564HCID 178434564, 화합물

생성물 1

HCID 69092482tert-butyl-3-(3-methyl-4-nitro-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate수율 35.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 3-methyl-4-nitro-1H-pyrazole (3.0 g, 23.6 mmol, 1.00 eq), tert-butyl-3-hydroxypyrrolidine-1-carboxylate (4.42 g, 23.6 mmol, 1.00 eq), and triphenylphosphine (6.19 g, 23.6 mmol, 1.00 eq) in THF (60 mL) was added a solution of diethyl azodicarboxylate (4.34 mL, 23.6 mmol, 1.00 eq) in THF (10 mL) in a drop-wise manner over 30 min. The reaction mixture was allowed to stir at ambient temperature for 20 hr and then concentrated. The crude reaction mixture was purified via repeated flash chromatography on silica gel eluting with a gradient of 0-35% EtOAc in heptane to give the title compound (2.48 g, 35% yield) as a colorless oil that was the early eluting of two structural isomers. 1H NMR (400 MHz, CDCl3) δ ppm 8.15 (s, 1 H) 4.80 (quin, J=5.7 Hz, 1 H) 3.83 (dd, J=6.0, 12.0 Hz, 1 H) 3.79-3.45 (m, 3 H) 2.52 (s, 3 H) 2.38 (q, J=7.0 Hz, 2 H) 1.46 (s, 9 H). m/z (APCI+) for C13H21N4O4 197.2 (M+H)+.

후처리

  1. concentrationconcentrated
  2. customThe crude reaction mixture
  3. customwas purified

출처 및 근거

ORD 기록
ord-133731aeda354787b31bb7314cbd0ffe
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290496B2

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