Acetone → HCID 59352227, compound

HRID 2385429Notes

Reaction equation

HRID 2385429 reaction equation
[CH3:1][C:2]([CH3:4])=O.[NH:5]1[CH2:10][CH2:9][O:8][CH:7]([CH2:11][N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]3([CH2:24][O:23][C:22]4[CH:25]=[C:26]5[C:30](=[CH:31][C:21]3=4)[CH2:29][CH2:28][O:27]5)[C:13]2=[O:32])[CH2:6]1.[Na]>ClC(Cl)C>[CH3:1][CH:2]([N:5]1[CH2:10][CH2:9][O:8][CH:7]([CH2:11][N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]3([CH2:24][O:23][C:22]4[CH:25]=[C:26]5[C:30](=[CH:31][C:21]3=4)[CH2:29][CH2:28][O:27]5)[C:13]2=[O:32])[CH2:6]1)[CH3:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5360545SodiumHCID 59352598HCID 59352598, compound

Product 1

HCID 59352227HCID 59352227, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of acetone (0.04 mL, 0.53 mmol) in dichloroethane (5 mL) was added 1′-(morpholin-2-ylmethyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.04 g, 0.11 mmol) and sodium triacetoxyhydroborate (0.11 g, 0.53 mmol), then the mixture was stirred at ambient temperature for 16 h. The reaction mixture was concentrated to dryness, and the residue was purified by flash chromatography with ethyl acetate/methanol/ammonium hydroxide (15/1/0.1) to afford 1′-{[4-(1-methylethyl)morpholin-2-yl]methyl}-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.02 g, 54%) as a colorless foam; 1H NMR (300 MHz, CDCl3) δ7.38-7.25 (m, 1H), 7.18-7.04 (m, 3H), 6.50 (s, 0.5H), 6.44 (s, 0.5H), 6.41 (s, 1H), 4.92 (d, J=9.0 Hz, 1H), 4.68 (d, J=9.0 Hz, 1H), 4.53 (t, J=8.7 Hz, 2H), 4.00-3.55 (m, 5H), 2.97 (t, J=8.7 Hz, 2H), 2.85-2.55 (m, 3H), 2.37-2.03 (m, 2H), 1.05-0.98 (m, 6H); MS (ES+) m/z 421.0 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was purified by flash chromatography with ethyl acetate/methanol/ammonium hydroxide (15/1/0.1)

Sources & evidence

ORD record
ord-9bef1a94f4944c73bbfde10caaee5b51
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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