tert-Butyl hydroperoxide → N-Cyclopropyl-3-propyloxirane-2-carboxamide

HRID 391491

반응식

HRID 391491 반응식
CC(C)[O-:3].[Sm+3].CC(C)[O-].CC(C)[O-].C1([As](=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[As](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OO)(C)(C)C.[CH:59]1([NH:62][C:63](=[O:69])/[CH:64]=[CH:65]/[CH2:66][CH2:67][CH3:68])[CH2:61][CH2:60]1>C1COCC1>[CH:59]1([NH:62][C:63]([CH:64]2[CH:65]([CH2:66][CH2:67][CH3:68])[O:3]2)=[O:69])[CH2:61][CH2:60]1

참가 물질

7

반응물 5

HCID 6410tert-Butyl hydroperoxideHCID 11773TriphenylarsineHCID 14382Triphenylarsine oxideHCID 2734138Samarium(III) isopropoxideHCID 25121219(E)-N-cyclopropylhex-2-enamide

생성물 1

HCID 24748482N-Cyclopropyl-3-propyloxirane-2-carboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
25 °C

실험 절차

A flask equipped with a stir bar, thermometer and addition funnel was placed under a nitrogen atmosphere then charged with samarium (III) isopropoxide (Sm(O-i-Pr)3, 430 mg, 1.3 mmol), triphenyl arsine oxide (Ph3As═O; 420 mg, 1.3 mmol), S-(−)1,1′-bi-2-naphthol ((S)-BINOL), 370 mg, 1.3 mmol), 4 Å molecular sieves (13 g) and THF (20 mL) then stirred for 30 min at 25±5° C. Tert-butyl hydroperoxide (2.8 mL, 5.5 M, 16 mmol) was then added. The mixture stirred for 30 minutes at 25±5° C., the amide of Example 4 (2.0 g, 13 mmol) in THF (2.0 mL) was then added. The reaction was stirred for 14 hours after which time the reaction had reached 95% completion as determined by HPLC.

후처리

  1. customA flask equipped with a stir bar
  2. additionthermometer and addition funnel
  3. stirringThe reaction was stirred for 14 hours after which time the reaction

출처 및 근거

ORD 기록
ord-8c07c7cf8b4247c98425dc1581934b62
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383858B2

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