Dimethylethylamine → HCID 67001706, compound

HRID 2279224Notes

Reaction equation

HRID 2279224 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 MNH4OH) 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 MNH4OH)
  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-23ca5ef49e4f40b2b632e1a57d92304d
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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