Triethylamine → tert-butyl 4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)-4-isocyanatopiperidine-1-carboxylate

HRID 711031노트

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HRID 711031 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:17][C:18]2[C:19]([I:26])=[N:20][N:21]([CH:23]([CH3:25])[CH3:24])[CH:22]=2)(C(O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:29]([CH2:32]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:41])C=CC=CC=1>C1(C)C=CC=CC=1>[I:26][C:19]1[C:18]([CH2:17][C:11]2([N:29]=[C:32]=[O:41])[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)=[CH:22][N:21]([CH:23]([CH3:24])[CH3:25])[N:20]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 674914961-(tert-butoxycarbonyl)-4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-4-carboxylic acid

생성물 1

HCID 86664613tert-butyl 4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)-4-isocyanatopiperidine-1-carboxylate수율 65.6%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
120 °C

실험 절차

To a solution of 1-(tert-butoxycarbonyl)-4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)piperidine-4-carboxylic acid (430 mg, 0.90 mmol) in toluene (10 mL) was added triethylamine (0.15 mL, 1.08 mmol) and diphenylphosphoryl azide (0.24 mL, 1.08 mmol). The mixture was heated at 120° C. for 3 hours, the volatiles were removed under reduced pressure and the resultant oil was purified by flash chromatography (7-60% ethyl acetate/heptanes, 25 g silica gel) to yield tert-butyl 4-((3-iodo-1-isopropyl-1H-pyrazol-4-yl)methyl)-4-isocyanatopiperidine-1-carboxylate (280 mg) as a clear oil. FT-IR (cm−1): 2253; 1H NMR (400 MHz, CDCl3, δ): 7.27 (s, 1H), 4.50 (m, 1H), 4.03 (br. s., 2H), 2.97 (br. s., 2H), 2.65 (s, 2H), 1.65 (m, 4H), 1.50 (s, 6H), 1.47 (s, 9H).

후처리

  1. customthe volatiles were removed under reduced pressure
  2. customthe resultant oil was purified by flash chromatography (7-60% ethyl acetate/heptanes, 25 g silica gel)

출처 및 근거

ORD 기록
ord-e4a3efa29c8f46879b002ef72ee46e8b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181252B2

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