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

HRID 1922513노트

반응식

HRID 1922513 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)=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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-befe0078bdd34b1d9af7952f7f1b9324
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173813B2

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