Ammonia → [7-(tert-Butyldimethylsilyloxy)-5,6,7,8-tetrahydronaphthalen-1-yl]thiourea

HRID 600817ノート

反応式

HRID 600817 の反応式
[C:1]([Si:5]([O:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([N:19]=[C:20]=[S:21])[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[NH3:22]>C1COCC1>[Si:5]([O:8][CH:9]1[CH2:10][C:11]2[C:12]([NH:19][C:20]([NH2:22])=[S:21])=[CH:13][CH:14]=[CH:15][C:16]=2[CH2:17][CH2:18]1)([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:7])[CH3:6]

参加物

4

反応物 2

HCID 222AmmoniaHCID 75581950Tert-butyl[(8-isothiocyanato-1,2,3,4-tetrahydronaphthalen-2-yl)oxy]dimethylsilane

生成物 1

HCID 86609617[7-(tert-Butyldimethylsilyloxy)-5,6,7,8-tetrahydronaphthalen-1-yl]thiourea

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of the product of Example 18C (1.25 g, 3.91 mmol) in THF (50 mL) was treated with 7N methanolic NH3 (5.6 mL, 3, 9.1 mmol), and the mixture was stirred at room temperature for 6 hours. The mixture was partitioned between EtOAc and H2O, and the separated organic phase was washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. Silica gel chromatography (98:2 to 95:5 CH2Cl2:CH3OH eluant) provided the title compound as a pale yellow solid, 1.27 g (97%). 1H NMR (300 MHz, DMSO-d6) δ 9.12 (s, 1H), 6.6-7.8 (br, 2H), 6.99-7.13 (m, 3H), 4.08 (m, 1H), 2.73-2.92 (m, 4H), 1.84-1.92 (m, 1H), 1.60-1.68 (m, 1H). MS (ESI+) m/z 337 (M+H).

後処理

  1. customThe mixture was partitioned between EtOAc and H2O
  2. washthe separated organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-1bd15e1e00484703b5784b8b002eab4d
出典データセット
uspto-grants-2011_03
特許番号
US07902236B2

反応ノート

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