Cyclopentanone → HCID 59263525, compound

HRID 425707Notes

Reaction equation

HRID 425707 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl.[NH:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]3([C:35]4=[CH:36][C:37]5[O:41][CH2:40][O:39][C:38]=5[CH:42]=[C:34]4[O:33][CH2:32]3)[C:24]2=[O:43])[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH:1]1([N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][N:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]4([C:35]5=[CH:36][C:37]6[O:41][CH2:40][O:39][C:38]=6[CH:42]=[C:34]5[O:33][CH2:32]4)[C:24]3=[O:43])[CH2:17][CH2:16]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 66642598HCID 66642598, compound

Product 1

HCID 59263525HCID 59263525, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of cyclopentanone (0.04 mL, 0.45 mmol) and triethyl amine (0.12 mL, 0.84 mmol) in dichloroethane (5.00 mL) was added 1′-(2-piperidin-4-ylethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one hydrochloride (0.12 g, 0.28 mmol) and sodium triacetoxyborohydride (0.10 g, 0.45 mmol). The reaction mixture was stirred for 16 hrs and concentrated in vacuo to dryness. The residue was subjected to flash chromatography eluting with ethyl acetate/methanol/ammonium hydroxide (15/1/0.1) to give 1′-[2-(1-cyclopentylpiperidin-4-yl)ethyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one as a white solid, which was treated with 4.0 M HCl in dioxane to give the title compound (0.05 g, 32% yield): mp 153-155° C.; 1H NMR (300 MHz, CD3OD) δ 7.37 (td, 1H), 7.21-7.08 (m, 3H), 6.53 (s, 1H), 6.11 (s, 1H), 5.88 (s, 1H), 5.87 (s, 1H), 4.83 (d, 1H), 4.69 (d, 1H), 3.98-3.75 (m, 2H), 3.68-3.38 (m, 3H), 3.01-2.83 (m, 2H), 2.25-2.08 (m, 4H), 1.92-1.37 (m, 11H); 13C NMR (75 MHz, CD3OD) δ 179.8, 157.6, 150.4, 143.8, 143.4, 133.6, 130.3, 124.9, 124.8, 120.8, 110.3, 103.7, 103.0, 94.3, 81.4, 69.1, 59.8, 53.2, 38.6, 34.3, 32.5, 30.6, 30.5, 29.4, 24.7; MS (ES+) m/z 461 (M+1).

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. washeluting with ethyl acetate/methanol/ammonium hydroxide (15/1/0.1)

Sources & evidence

ORD record
ord-0eceac45ef654e56b8225eb365ea9405
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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