Cyclopentanone → HCID 59263525, compound

HRID 1259800Notes

Reaction equation

HRID 1259800 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-3463acb1199849719ab90c0857d4a25b
Source dataset
uspto-grants-2013_06
Patent number
US08466188B2

Reaction notes

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