Aluminium lithium hydride → HCID 56593709, compound

HRID 1668494Notes

Reaction equation

HRID 1668494 reaction equation
[CH3:1][N:2]1[C:6](=O)[CH2:5][CH:4]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([NH:17][C:18](=O)[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[C:3]1=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:18]([NH:17][C:13]1[CH:12]=[C:11]2[C:16]([C:8]([CH:4]3[CH2:5][CH2:6][N:2]([CH3:1])[CH2:3]3)=[CH:9][NH:10]2)=[CH:15][CH:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 56595719HCID 56595719, compound

Product 1

HCID 56593709HCID 56593709, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 115 (2.28 g, 6.563 mmol) in dry THF (30 mL) was treated with LiAlH4 (2.49 g, 65.636 mmol) portion wise over a period of 45 min. at 0° C. The reaction was brought to room temperature and stirred for 48 h. The reaction was quenched with sodium sulfate decahydrate (8.0 g) followed by careful addition of water (9 mL) at 0° C. and stirred for 30 min. at room temperature. The reaction was diluted with ethyl acetate (50 mL), filtered and washed with ethyl acetate (2×50 mL). The combined ethyl acetate layer was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 5:95 to 1:9) to obtain compound 116 (0.44 g, 22%) as a foam. 1H NMR (DMSO-d6) δ 1.76-1.87 (m, 1H), 2.11-2.23 (m, 1H), 2.27 (s, 3H), 2.36 (t, 1H, J=8.4 Hz), 2.42-2.48 (m, 1H), 2.64-2.71 (m, 1H), 2.90 (t, 1H, J=8.1 Hz), 3.37-3.45 (m, 1H), 4.26 (d, 2H, J=5.7 Hz), 5.88 (t, 1H, J=6.0 Hz), 6.34 (d, 1H, J=0.9 Hz), 6.45 (dd, 1H, J=1.8, 8.4 Hz), 6.72 (d, 1H, J=1.2 Hz), 7.17-7.38 (m, 6H), 10.11 (s, 1H); ESI-MS (m/z, %) 306 (MH+, 100); ESI-HRMS calculated for C20H24N3 (MH+), calculated: 306.1964, observed: 306.1967.

Workup

  1. customwas brought to room temperature
  2. customThe reaction was quenched with sodium sulfate decahydrate (8.0 g)
  3. additionfollowed by careful addition of water (9 mL) at 0° C.
  4. stirringstirred for 30 min. at room temperature
  5. additionThe reaction was diluted with ethyl acetate (50 mL)
  6. filtrationfiltered
  7. washwashed with ethyl acetate (2×50 mL)
  8. customThe combined ethyl acetate layer was evaporated
  9. customcrude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 5:95 to 1:9)

Sources & evidence

ORD record
ord-da88d95c64cb4d678100e21b47c65bd0
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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