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

HRID 1922513ノート

反応式

HRID 1922513 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)=C[CH:27]=2)CC1.[C:33]([OH:36])(=O)[CH3:34].[BH3-]C#N.[Na+].[OH-:41].[Na+]>CO>[O:41]1[C:23]2([CH2:5][CH2:6][CH:7]([N:8]3[C:9]4[C:4](=[CH:3][CH:2]=[CH:11][CH:10]=4)[CH2:13][CH2:12]3)[CH2:27][CH2:28]2)[O:36][CH2:33][CH2:34]1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 573433941-(6-Bromo-3,4-dihydro-1(2H)-quinolinyl)-2-chloroethanoneHCID 58289996HCID 58289996、化合物

生成物 1

HCID 598070311-(1,4-Dioxaspiro[4.5]decan-8-yl)indoline収率 81%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of compound 1 (2.0 g, 16.78 mmol) and compound 2 (3.15 g, 20.139 mmol) in dry methanol (20 mL) was treated with acetic acid (2.4 mL, 42.00 mmol) followed by NaCNBH3 (1.26 g, 20.14 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 (50 mL) and product was extracted into ethyl acetate (2×50 mL). The combined ethyl acetate layer was washed with brine (25 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 (3.52 g, 81%) as a solid. 1H NMR (CDCl3) δ 7.06-7.02 (m, 2H), 6.59 (t, J=14.7 Hz, 1H), 6.42 (d, J=8.1 Hz, 1H), 3.46 (s, 4H), 3.46-3.35 (m, 3H), 2.93 (t, J=16.5 Hz, 2H), 1.87-1.60 (m, 8H). MS-ESI (m/z, %): 262 (8), 260 (MH+, 100), 120 (28).

後処理

  1. customwas brought to room temperature
  2. extractionwas extracted into ethyl acetate (2×50 mL)
  3. washThe combined ethyl acetate layer was washed with brine (25 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-befe0078bdd34b1d9af7952f7f1b9324
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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