Water → 8-{5-[4-(Trifluoromethyl)phenyl]oxazol-2-ylamino}-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 600775ノート

反応式

HRID 600775 の反応式
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:24]=3[CH2:23][C:22](=[O:25])[CH2:21][CH2:20]4)=[N:11][CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+].O>C(O)C>[F:27][C:2]([F:1])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:24]=3[CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]4)=[N:11][CH:10]=2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 119558408-{5-[4-(Trifluoromethyl)phenyl]oxazol-2-ylamino}-3,4-dihydronaphthalen-2(1H)-one

生成物 1

HCID 119642558-{5-[4-(Trifluoromethyl)phenyl]oxazol-2-ylamino}-1,2,3,4-tetrahydronaphthalen-2-ol収率 56.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

The product of Example 1I (60 mg, 0.161 mmol) in ethanol (6 mL) was treated at 0° C. with NaBH4 (7 mg, 0.184 mmol). The reaction was stirred at 0° C. for 1 hour and was then poured into H2O and extracted with ethyl acetate. The extracts were dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 70%-85% ethyl acetate-hexane to afford the title compound as a tan solid (34 mg, 56%). 1H NMR (DMSO-d6) δ 9.33 (s, 1H), 7.78 (m, 4H), 7.62 (s, 1H), 7.55 (d, 1H, J=7.4 Hz), 7.11 (m, 1H), 6.88 (d, 1H, J=7.2 Hz), 4.83 (d, 1H, J=4.1 Hz), 3.92 (m, 1H), 2.69-2.98 (m, 4H), 1.86 (m, 1H), 1.62 (m, 1H); MS (ESI+) m/z 375 (M+H).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 70%-85% ethyl acetate-hexane

出典と根拠

ORDレコード
ord-8bf866afe58340a190e1428e2f932e2c
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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