Lithium Hydroxide → (2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol

HRID 1672543ノート

反応式

HRID 1672543 の反応式
CO[C@H](C1C=CC=CC=1)C([O:6][C@@H:7]1[CH2:16][CH2:15][C:14]2[C:9](=[C:10]([NH2:17])[CH:11]=[CH:12][CH:13]=2)[CH2:8]1)=O.[OH-].[Li+]>O1CCCC1>[NH2:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH2:8][C@H:7]([OH:6])[CH2:16][CH2:15]2

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 91257777HCID 91257777、化合物

生成物 1

HCID 57936087(2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of Example 24D (3.05 g, 9.80 mmol) in tetrahydrofuran (40 mL) and lithium hydroxide (1 M aq, 30 mL, 30.0 mmol) was stirred vigorously at ambient temperature. After 1.5 hours the reaction mixture was partitioned between 100 mL ethyl acetate:H2O (1:1). The separated organic phase was washed with aq saturated NaHCO3 and brine, dried over Na2SO4, and filtered. The solvent was removed at the rotary evaporator to yield 1.31 g (82% yield) of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 6.76 (t, 1H), 6.41 (d, 1H), 6.28 (d, 1H), 4.74, (d, 1H), 4.65 (bs, 2H), 3.90 (m, 1H), 2.52-2.79 (m, 3H), 2.16 (m, 1H), 1.83 (m, 1H), 1.55 (m, 1H). MS (DCI+) m/z 164 (M+H)+, 181 (M+NH4)+.

後処理

  1. customAfter 1.5 hours the reaction mixture was partitioned between 100 mL ethyl acetate:H2O (1:1)
  2. washThe separated organic phase was washed with aq saturated NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was removed at the rotary evaporator

出典と根拠

ORDレコード
ord-6a75acd2fc6a4656b9829fd1d85c597f
出典データセット
uspto-grants-2011_08
特許番号
US07998993B2

反応ノート

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