4-Phenoxybenzaldehyde → HCID 59263537, compound

HRID 545940Notes

Reaction equation

HRID 545940 reaction equation
[O:1]=[C:2]1[C:10]2([C:14]3=[CH:15][C:16]4[O:20][CH2:19][O:18][C:17]=4[CH:21]=[C:13]3[O:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:22][CH2:23][CH:24]=O.[NH2:26][CH2:27][CH:28]1[CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C1(OC2C=CC(C=O)=CC=2)C=CC=CC=1>C1COCC1.CCOCC>[CH:28]1([CH2:27][NH:26][CH2:24][CH2:23][CH2:22][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]3([C:14]4=[CH:15][C:16]5[O:20][CH2:19][O:18][C:17]=5[CH:21]=[C:13]4[O:12][CH2:11]3)[C:2]2=[O:1])[CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 661394-PhenoxybenzaldehydeHCID 75646CyclopropanemethanamineHCID 2724942TriacetoxyborohydrideHCID 86609017HCID 86609017, compound

Product 1

HCID 59263537HCID 59263537, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2′-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-1′(2′H)-yl)propanal (0.07 g, 0.20 mmol) in THF (5.00 mL) was added (aminomethyl)cyclopropane (0.30 mmol) and MP-triacetoxyborohydride (0.26 g, 0.60 mmol). After overnight shaking, the polymer-bound 4-phenyloxybenzaldehyde (0.25 g, 0.18 mmol) was added. After another overnight shaking, the mixture was diluted with ether (10.0 mL) and filtered. The filtrate was concentrated in vacuo to dryness. The residue was recrystallized to give the title compound (0.05 g) in 62% yield as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.32-6.92 (m, 4H), 6.49 (s, 1H), 6.12 (s, 1H), 5.83 (m, 2H), 4.86 (m, 1H), 4.64 (m, 1H), 3.97-3.77 (m, 2H), 2.87-2.80 (m, 2H), 2.66-2.56 (m, 2H), 1.02-0.94 (m, 1H), 0.56-0.47 (m, 2H), 0.25-0.18 (m, 2H); MS (ES+) m/z 393.3 (M+1).

Workup

  1. stirringAfter another overnight shaking
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo to dryness
  4. customThe residue was recrystallized

Sources & evidence

ORD record
ord-5716b650fd5644a09997e36441f863f7
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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