Vinyl isobutyl ether → HCID 54165959, 화합물

HRID 428320

반응식

HRID 428320 반응식
[CH:1]([N:4]([CH:29]([CH3:31])[CH3:30])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:19]=[C:18](Br)[CH:17]=[CH:16][C:15]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:39]([O:43]C=C)[CH:40](C)C.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:1]([N:4]([CH:29]([CH3:31])[CH3:30])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:19]=[C:18]([C:39](=[O:43])[CH3:40])[CH:17]=[CH:16][C:15]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 7992Vinyl isobutyl etherHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 24885301(R)-3-(2-benzyloxy)-5-bromophenyl)-N,N-diisopropyl-3-phenylpropan-1-amine

생성물 1

HCID 54165959HCID 54165959, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of (R)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropanamine (Example 12) (10.2 g, 21.23 mmol) in DMF (100 mL) under nitrogen atmosphere at room temperature were sequentially added triethylamine (2.58 g, 25.47 mmol), TlOAc (6.15 g, 23.35 mmol), isobutylvinylether (14 mL, 106.14 mmol), DPPP (0.87 g, 2.12 mmol) and Pd(OAc)2 (0.24 g, 1.06 mmol). The reaction temperature was raised to 100° C. and stirred for 3 hours, cooled to room temperature, filtered and treated with HCl (5%, 250 mL) and stirred for another 2 hours. The reaction mixture was repeatedly extracted with dichloromethane and the combined organic layers were dried (MgSO4), filtered and the solvent evaporated. Triethylamine and DMF were destined off under reduced pressure to yield 9 g (98%); 1H NMR (CDCl3) δ1.22 (m, 12H), 2.52-2.70 (m, 7H), 3.40 (br, 2H), 4.34 (t, 1H), 5.10 (s, 1H), 6.90 (d, 1H), 7.17-7.40 (m, 10H), 7.82 (m, 1H) and 7.92 (s, 1H).

후처리

  1. customat room temperature
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. additiontreated with HCl (5%, 250 mL)
  5. stirringstirred for another 2 hours
  6. extractionThe reaction mixture was repeatedly extracted with dichloromethane
  7. dry with materialthe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. customto yield 9 g (98%)

출처 및 근거

ORD 기록
ord-1c4499c960ae4932a4e9ac8d078bc00c
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313132B1

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