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 629832ノート

反応式

HRID 629832 の反応式
[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

参加物

5

反応物 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

生成物 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]isoquinoline収率 55.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6a5f7b5cc5af4089a738361e7a24b2ca
出典データセット
uspto-grants-2016_04
特許番号
US09315514B2

反応ノート

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