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Diiodomethane → (R)-4-(Cyclopropylmethyl)-5-(quinolin-8-ylsulfonyl)-3,4,5,6-tetrahydro-1H-benzo[f][1,4]oxazocine

HRID 1429386
ノート
印刷プレビュー

反応式

HRID 1429386 の反応式
[CH2:1]([C@H:4]1[N:11]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)(=[O:14])=[O:13])[CH2:10][C:9]2[CH:25]=[CH:26][CH:27]=[CH:28][C:8]=2[CH2:7][O:6][CH2:5]1)[CH:2]=[CH2:3].[CH2:29]([Zn]CC)C.ICI.[Cl-].[NH4+]>C1COCC1>[CH:2]1([CH2:1][C@H:4]2[N:11]([S:12]([C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:24]=3[N:23]=[CH:22][CH:21]=[CH:20]4)(=[O:14])=[O:13])[CH2:10][C:9]3[CH:25]=[CH:26][CH:27]=[CH:28][C:8]=3[CH2:7][O:6][CH2:5]2)[CH2:29][CH2:3]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 86677162(R)-4-Allyl-5-(quinolin-8-ylsulfonyl)-3,4,5,6-tetrahydro-1H-benzo[f][1,4]oxazocineHCID 178418750HCID 178418750、化合物

生成物 1

HCID 71269531(R)-4-(Cyclopropylmethyl)-5-(quinolin-8-ylsulfonyl)-3,4,5,6-tetrahydro-1H-benzo[f][1,4]oxazocine収率 31%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of compound 18 (100 mg, 0.25 mmol) in dry THF (5 mL) was added diethyl zinc (1M solution in hexane, 2.5 mL) at 0° C. under nitrogen atmosphere followed by diiodomethane (667 mg, 2.5 mmol). The reaction was stirred at 0° C. for 6 h and poured over cold aqueous solution of ammonium chloride. The organic layer was separated and the aqueous layer extracted repeatedly with EA. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by Prep-TLC to afford the compound 20 (32 mg, 31% yield). 1H NMR (500 MHz, CDCl3) δ 8.94 (m, 1H), 8.47 (d, J=7.5 Hz, 1H), 8.13 (d, J=8.0 Hz, 1H), 7.93 (d, J=8.5 Hz, 1H), 7.55 (t, J=8.0 Hz, 1H), 7.43 (dd, J=8.0 Hz, 4.0 Hz 1H), 7.17 (d, J=7.5 Hz, 1H), 6.98 (t, J=7.5 Hz, 1H), 6.89 (m, 1H), 6.80 (d, J=7.5 Hz, 1H), 5.07 (d, J=15.5 Hz, 1H), 4.95 (d, J=15.0 Hz, 1H), 4.86 (d, J=15.5 Hz, 1H), 4.60 (d, J=15.0 Hz, 1H), 4.49 (m, 1H), 4.14 (d, J=12.0 Hz, 1H), 3.75 (d, J=12.0 Hz, 1H), 1.71 (m, 1H), 1.10 (m, 1H), 0.63 (m, 1H), 0.33 (m, 2H), −0.11 (m, 2H). MS (ESI+) m/z: 409 [M+H]+. LCMS (m/z): 409.2 (MH+).

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted repeatedly with EA
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by Prep-TLC

出典と根拠

ORDレコード
ord-7dfe3f3a592946c49df6a7c2cc53e22e
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08940722B2

反応ノート

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