Potassium hydride → 5-cinnamyloxymethyl-3-cyclopropylmethyl-9-methoxy-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one

HRID 35528

반응식

HRID 35528 반응식
[H-].[K+].[CH:3]1([CH2:6][N:7]2[CH2:16][CH2:15][C:14]34[C:17]5[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:18]=5[O:19][CH:13]3[CH:12]3[CH2:26][CH2:27][C:9]4([CH:10]([CH2:28][OH:29])[CH2:11]3)[C:8]2=[O:30])[CH2:5][CH2:4]1.C1(CN2[CH2:44][CH2:43][C:42]34C5C=CC=C(OC)C=5OC3[CH:40]3[CH2:54][CH2:55][C:37]4([CH:38](C(OC)=O)[CH2:39]3)C2=O)CC1.C(Br)C=CC1C=CC=CC=1>O1CCCC1.C(Cl)Cl.O.CCCCCC>[CH2:44]([O:29][CH2:28][CH:10]1[C:9]23[CH2:27][CH2:26][CH:12]([CH:13]4[O:19][C:18]5[C:20]([O:24][CH3:25])=[CH:21][CH:22]=[CH:23][C:17]=5[C:14]42[CH2:15][CH2:16][N:7]([CH2:6][CH:3]2[CH2:5][CH2:4]2)[C:8]3=[O:30])[CH2:11]1)[CH:43]=[CH:42][C:37]1[CH:55]=[CH:54][CH:40]=[CH:39][CH:38]=1

참가 물질

9

반응물 4

HCID 82127Potassium hydrideHCID 98116BromomethylstyreneHCID 212944573-cyclopropylmethyl-9-methoxy-5-methoxycarbonyl-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-oneHCID 212944613-cyclopropylmethyl-5-hydroxymethyl-9-methoxy-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one

생성물 1

HCID 704165665-cinnamyloxymethyl-3-cyclopropylmethyl-9-methoxy-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one

시약·촉매·용매 4

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

To a solution of 2.06 g of 35% potassium hydride in oil, prewashed with hexane, in 15 mL of tetrahydrofuran was added 0.70 g of 3-cyclopropylmethyl-5-hydroxymethyl-9-methoxy-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one (synthesized by following the procedures of Example 1, Method A, using 3-cyclopropylmethyl-9-methoxy-5-methoxycarbonyl-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one, U.S. Pat. No. 4,477,456, as the starting material) and the mixture was heated under reflux for 30 min. Cinnamyl bromide (2 mL) was added to the cooled mixture which was then heated under reflux for 20 minutes. Water and methylene chloride were added, and the aqueous layer was extracted with methylene chloride. Removal of the solvent from the dried organic phases gave 0.84 of 5-cinnamyloxymethyl-3-cyclopropylmethyl-9-methoxy-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one. NMR spectrum (δ in CDCl3): 7.1-7.4 (m, 5H); 6.8 (m, 2H); 6.7 (m, 1H); 6.6 (d, J=15 Hz, 1H); 6.3 (d/t, J=15/7 Hz, 1H), 4.4 (s, 1H); 5.8 (m, 2H); 3.9 (s, 3H); 0.5 (m, 2H); and 0.2 (m, 2H), among others.

후처리

  1. customsynthesized
  2. temperature4,477,456, as the starting material) and the mixture was heated
  3. temperatureunder reflux for 30 min
  4. temperaturewas then heated
  5. temperatureunder reflux for 20 minutes
  6. extractionthe aqueous layer was extracted with methylene chloride
  7. customRemoval of the solvent from the dried organic phases

출처 및 근거

ORD 기록
ord-7ed96d5c211b4ecca6f4426ef547f4ce
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04767764

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