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

HRID 1922520노트

반응식

HRID 1922520 반응식
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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-086cec33c2684060b1948c6763438a05
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173813B2

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