Dimethylethylamine → HCID 67001706, compound

HRID 1186226Notes

Reaction equation

HRID 1186226 reaction equation
CN(CC)C.[CH2:6]([N:13]1[CH2:35][CH2:34][N:16]2[C:17]3[CH:33]=[CH:32][CH:31]=[CH:30][C:18]=3[N:19]([C:22]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=O)[CH2:20][CH2:21][CH:15]2[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCCC1>[CH2:6]([N:13]1[CH2:35][CH2:34][N:16]2[C:17]3[CH:33]=[CH:32][CH:31]=[CH:30][C:18]=3[N:19]([CH2:22][C:24]3[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=3)[CH2:20][CH2:21][CH:15]2[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 11723DimethylethylamineHCID 67002093HCID 67002093, compound

Product 1

HCID 67001706HCID 67001706, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of alane-N,N-dimethylethylamine complex (Aldrich, 0.5 M in toluene, 3.1 mL, 1.55 mmol) was added dropwise with stirring to an ice-cooled solution of the product of Example 43 (123 mg, 0.309 mmol) in tetrahydrofuran (10 mL). The mixture was stirred under nitrogen as the ice bath was allowed to expire over 2.5 hours. The reaction was quenched by addition of methanol (2 mL) and concentrated under vacuum. The residue was purified by flash chromatography (SiO2, eluted with CH2Cl2-methanol-15 M NH4OH) and then by HPLC (30×100 mm, C18, Waters XBridge™ column eluting with aqueous 0.1 M (NH4)2CO3-methanol (80:20-0:100 over 15 minutes)) to provide the title compound: 1H NMR (300 MHz, CD3OD) δ ppm 1.60 (ddt, J=15.3, 2.4 Hz, 1H), 1.85-2.03 (m, 1H), 2.26 (t, J=10.7 Hz, 1H), 2.37 (td, J=11.1, 3.2 Hz, 1H), 2.70 (br d, J=10.7 Hz, 1H), 2.86-2.98 (m, 3H), 3.06 (dt, J=11.5, 2.8 Hz, 1H), 3.25-3.35 (m, 1H), 3.55 (td, J=11.4, 2.2 Hz, 1H), 3.61 (s, 2H), 4.32 (d, J=16.7 Hz, 1H), 4.61 (d, J=16.7 Hz, 1H), 6.75 (dd, J=6.8, 2.4 Hz, 1H), 6.78-6.92 (m, 2H), 6.94 (dd, J=7.1, 2.1 Hz, 1H), 7.24-7.39 (m, 5H), 7.42 (d, J=5.9 Hz, 2H), 8.40 (d, J=6.3 Hz, 2H); MS (ESI) m/z 385 (M+H)+.

Workup

  1. customThe reaction was quenched by addition of methanol (2 mL)
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by flash chromatography (SiO2, eluted with CH2Cl2-methanol-15 M NH4OH)
  4. washby HPLC (30×100 mm, C18, Waters XBridge™ column eluting with aqueous 0.1 M (NH4)2CO3-methanol (80:20-0:100 over 15 minutes))

Sources & evidence

ORD record
ord-b68ffcf3d95e4e81b4da4b525a70ef05
Source dataset
uspto-grants-2014_03
Patent number
US08673896B2

Reaction notes

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