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

HRID 1922520Notes

Reaction equation

HRID 1922520 reaction equation
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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-086cec33c2684060b1948c6763438a05
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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