Dimethylamine → HCID 68600521, compound

HRID 1407822Notes

Reaction equation

HRID 1407822 reaction equation
[O:1]=[C:2]1[C:10]2([CH2:14][O:13][C:12]3[CH:15]=[C:16]4[C:20](=[CH:21][C:11]2=3)[CH2:19][CH2:18][O:17]4)[C:9]2[C:8]([CH:22]=O)=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]1[CH2:24][C@H:25]1[CH2:29][CH2:28][CH2:27][O:26]1.[CH3:30][NH:31][CH3:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:30][N:31]([CH2:22][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[C:10]1([CH2:14][O:13][C:12]3[CH:15]=[C:16]4[C:20](=[CH:21][C:11]1=3)[CH2:19][CH2:18][O:17]4)[C:2](=[O:1])[N:3]2[CH2:24][C@H:25]1[CH2:29][CH2:28][CH2:27][O:26]1)[CH3:32]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86642197HCID 86642197, compound

Product 1

HCID 68600521HCID 68600521, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of 2′-oxo-1′-[(2R)-tetrahydrofuran-2-ylmethyl]-1′,2′,5,6-tetrahydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indole]-4′-carbaldehyde (0.10 g, 0.26 mmol) and dimethylamine (0.19 mL, 0.38 mmol) in dichloroethane was added sodium triacetoxyborohydride (0.10 g, 0.46 mmol) at 0° C. The mixture was stirred at ambient temperature for 18 h, and quenched with water. The mixture was extracted with ethyl acetate (3×20 mL). The combined organic solution was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was subjected to column chromatography (methanol/ethyl acetate, 5/100) to afford 4′-[(dimethylamino)methyl]-1′-[(2R)-tetrahydrofuran-2-ylmethyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.05 g, 46%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ7.29-7.20 (m, 1H), 7.07 (d, J=7.9 Hz, 1H), 6.98 (t, J=7.0 Hz, 1H), 6.45-6.39 (m, 1H), 6.38 (s, 1H), 5.07 (dd, J=8.8, 2.1 Hz, 1H), 4.88 (d, J=8.8 Hz, 1H), 4.52 (t, J=8.6 Hz, 1H), 4.33-4.21 (m, 1H), 3.98-3.62 (m, 4H), 3.33 (dd, J=13.2, 3.3 Hz, 1H), 3.03-2.88 (m, 2H), 2.80 (d, J=13.2 Hz, 1H), 2.09-1.63 (m, 10H); MS (ES+) m/z 421.0 (M+1).

Workup

  1. customquenched with water
  2. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic solution was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8e6b417a629144f69085518c13cc74a6
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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