Water → 1-[2-(4,5-Diphenyloxazol-2-yl)pyrrolidin-1-yl]-2-hydroxy-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

HRID 1741385노트

반응식

HRID 1741385 반응식
[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH2:22][CH2:21][CH2:20][NH:19]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:23]([O:40][C:41]1[CH:50]=[CH:49][CH:48]=[C:47]2[C:42]=1[CH2:43][CH2:44][CH:45]1[O:51][CH:46]12)([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)(=O)C.O>O1CCCC1>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH2:22][CH2:21][CH2:20][N:19]3[CH:46]3[C:47]4[C:42](=[C:41]([O:40][Si:23]([C:36]([CH3:38])([CH3:37])[CH3:39])([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[CH:50]=[CH:49][CH:48]=4)[CH2:43][CH2:44][CH:45]3[OH:51])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 183672762-(4,5-Diphenyloxazol-2-yl)pyrrolidineHCID 183674385-Tert-butyldiphenylsilyloxy-1,2-epoxy-1,2,3,4-tetrahydronaphthalene

생성물 1

HCID 183673291-[2-(4,5-Diphenyloxazol-2-yl)pyrrolidin-1-yl]-2-hydroxy-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene수율 30%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-(4,5-diphenyloxazol-2-yl)pyrrolidine (0.66 g) and 5-tert-butyldiphenylsilyloxy-1,2-epoxy-1,2,3,4-tetrahydronaphthalene (0.6 g) in tetrahydrofuran (10 ml) was added Ti[O-CH(CH3)2 ]4 (0.66 ml) at room temperature. After being stirred for 5 days at the same temperature, the mixture was poured into the mixture of ethyl acetate and water. The organic layer was washed with water and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-[2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-2-hydroxy-5-tert-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (0.31 g). MS (m/z): 691 (M+) IR (Neat): 3300 cm-1NMR (CDCl3, δ): 1.07 (9H, s), 1.7-2.4 (6H, m), 2.6-3.3 (2H, m), 3.4-3.6 (2H, m), 4.1-4.4 (2H, m), 6.28 (1H, d, J=8.0 Hz), 6.75 (1H, t, J=8.0 Hz), 6.88 (1H, d, J=8.0 Hz), 7.3-7.8 (20H, m)

후처리

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-60fe60aaafef4eb7a9cb881b2b5df5e1
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05972965

반응 노트

불러오는 중…