Benzyl Bromide → (4bS,8R,8aS,9aR,10S,13aR,13bR)-1-benzyloxy-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinoline

HRID 629832노트

반응식

HRID 629832 반응식
[C:1]([C@:5]1([CH3:34])[C@@H:18]2[C@@:9]3([CH2:20][CH2:19][C@:16]4([CH2:17]2)[C@@:11]25[C:27]6[C:22](=[CH:23][CH:24]=[C:25]([OH:29])[C:26]=6[O:28][C@@H:10]32)[CH2:21][C@H:15]4[N:14]([CH2:30][CH:31]2[CH2:33][CH2:32]2)[CH2:13][CH2:12]5)[O:8][CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:41](Br)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CC(C)=O>[CH2:41]([O:29][C:25]1[C:26]2[O:28][C@H:10]3[C@@:9]45[CH2:20][CH2:19][C@:16]6([CH2:17][C@@H:18]4[C@:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:34])[O:6][CH2:7][O:8]5)[C@@:11]43[CH2:12][CH2:13][N:14]([CH2:30][CH:31]3[CH2:32][CH2:33]3)[C@@H:15]6[CH2:21][C:22]([C:27]=24)=[CH:23][CH:24]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 73211769(4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol

생성물 1

HCID 121278739(4bS,8R,8aS,9aR,10S,13aR,13bR)-1-benzyloxy-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinoline수율 55.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a suspension of compound 3 (1.0 g, 2.15 mMol) and K2CO3 (0.88 g, 6.45 mMol) in acetone (10 ml) was added benzyl bromide (0.31 mL, 2.15 mMol). The resulting suspension was stirred at ambient temperature for 24 h. All volatiles were removed by vacuum distillation. The crude product was purified by column chromatography on silica to give 0.66 g of the title compound 7 (54.5% yield) in a purity of 96.9% as a white solid.

후처리

  1. customAll volatiles were removed by vacuum distillation
  2. customThe crude product was purified by column chromatography on silica

출처 및 근거

ORD 기록
ord-6a5f7b5cc5af4089a738361e7a24b2ca
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315514B2

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