Water → (S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate

HRID 1254341

반응식

HRID 1254341 반응식
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:34]([O:38][C:39]([NH:41][C@H:42]([CH2:45][O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48])[CH2:43]O)=[O:40])([CH3:37])([CH3:36])[CH3:35].O>C1COCC1.CC#N.C1COCC1>[Si:47]([O:46][CH2:45][CH:42]1[CH2:43][N@@:41]1[C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48]

참가 물질

7

반응물 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11141286HCID 11141286, 화합물

생성물 1

HCID 72525716(S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate수율 54.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 22177404Acetonitrile tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Ph3P (19.65 g, 75 mmol) was dissolved in 9:1 THF/CH3CN (600 mL) and cooled to 0° C., DIAD (14.7 mL, 75 mmol) was added dropwise over 15 min. After stirring for 30 min, a solution of (S)-2-(t-butoxycarbonylamino)-3-(t-butyldimethylsilyloxy)propan-1-ol (15.25 g, 50 mmol) in THF (100 mL) was added dropwise over 15 min, the reaction mixture was allowed to rt and stirred for 24 h. Water (100 mL) was added and volatiles were evaporated. The residue was partitioned between water (100 mL) and EtOAc (2×100 mL). The organic layers were washed with brine, dried over MgSO4 and evaporated. The residue was purified by silica chromatography to provide (S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate (7.8 g, 54%) as an oil. 1H NMR (CDCl3, 400 MHz): δ 0.07 (s, 6 H), 0.89 (s, 9 H), 1.45 (s, 9 H), 2.06 (d, J=3.6 Hz 1 H), 2.26 (d, J=6 Hz 1 H), 2.55 (m, 1 H), 3.64 (dd, J=16.4, 4.8 Hz, 1 H), 3.82 (dd, J=16.4, 4.4 Hz, 1 H).

후처리

  1. customwas allowed to rt
  2. stirringstirred for 24 h
  3. customvolatiles were evaporated
  4. customThe residue was partitioned between water (100 mL) and EtOAc (2×100 mL)
  5. washThe organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by silica chromatography

출처 및 근거

ORD 기록
ord-066d8ceda0d84528aca1a4f1bc5192e0
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455521B2

연결된 노트

불러오는 중…