Acetic Acid → 1-(1,4-Dioxaspiro[4.5]decan-8-yl)-1,2,3,4-tetrahydroquinoline

HRID 1922520ノート

反応式

HRID 1922520 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=O)[CH2:13]Cl)[CH2:7][CH2:6][CH2:5]2.CN(C)CCN1[C:28]2[C:23](=CC([N+]([O-])=O)=[CH:26][CH:27]=2)CC1.[C:33]([OH:36])(=O)[CH3:34].C(O[BH-](OC(=O)C)OC(=O)C)(=[O:39])C.[Na+].[OH-].[Na+]>ClCCCl>[O:39]1[C:28]2([CH2:23][CH2:13][CH:12]([N:8]3[C:9]4[C:4](=[CH:3][CH:2]=[CH:11][CH:10]=4)[CH2:5][CH2:6][CH2:7]3)[CH2:26][CH2:27]2)[O:36][CH2:33][CH2:34]1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 573433941-(6-Bromo-3,4-dihydro-1(2H)-quinolinyl)-2-chloroethanoneHCID 58289996HCID 58289996、化合物

生成物 1

HCID 598070451-(1,4-Dioxaspiro[4.5]decan-8-yl)-1,2,3,4-tetrahydroquinoline収率 53.6%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

A solution of compound 1 (0.2 g, 1.502 mmol) and compound 2 (0.28 g, 1.802 mmol) in dry 1,2-dichloroethane (5 mL) was treated with acetic acid (0.085 mL, 1.502 mmol) followed by sodium triacetoxyborohydride (0.38 g, 1.802 mmol) at 0° C. The resulting mixture was brought to room temperature and stirred for 3 h. The reaction was basified with 1 N NaOH solution (20 mL) and the product was extracted into ethyl acetate (2×20 mL). The combined ethyl acetate layer was washed with brine (15 mL) and dried (Na2SO4). The solvent was evaporated and the crude product was purified by column chromatography (ethyl acetate:hexanes, 1:4) to obtain compound 3 (0.22 g, 53.6%) as a syrup. 1H NMR (CDCl3) δ 7.06 (t, 1H, J=7.8 Hz), 6.95 (d, 1H, J=7.2 Hz), 6.67-6.55 (m, 2H), 3.96 (s, 4H), 3.72-3.63 (m, 1H), 3.21 (t, 2H, J=5.4 Hz), 2.72 (t, 2H, J=6.3 Hz), 1.92-1.63 (m, 10H); ESI-MS (m/z, %) 274 (MH+, 100).

後処理

  1. customwas brought to room temperature
  2. extractionthe product was extracted into ethyl acetate (2×20 mL)
  3. washThe combined ethyl acetate layer was washed with brine (15 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe crude product was purified by column chromatography (ethyl acetate:hexanes, 1:4)

出典と根拠

ORDレコード
ord-086cec33c2684060b1948c6763438a05
出典データセット
uspto-grants-2012_05
特許番号
US08173813B2

反応ノート

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