HCID 10158726, compound → HCID 9967220, compound

HRID 412997Notes

Reaction equation

HRID 412997 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][NH:13][C:14](=O)OC(C)(C)C)=[CH:8][C:7]([S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])=[CH:6][CH:5]=2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:14][NH:13][CH2:12][CH2:11][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:22])=[O:23])[CH:8]=2)[NH:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 10158726HCID 10158726, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9967220HCID 9967220, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl 2-[2-methyl-5-(phenylsulfonyl)-1H-indol-3-yl]ethylcarbamate (0.46 g, 1.10 mmol) in THF (2.0 mL) was added to a slurry of LiAlH4 (0.47 g, 12.3 mmol) in THF (4.0 mL) and the mixture was heated to reflux for 6.5 hours. The reaction was cooled to room temperature and quenched with water (12.0 mL) and 15% NaOH (12.0 mL). The mixture was filtered through diatomaceous earth and the filtrate was concentrated in vacuo. The residue was extracted with CH2Cl2, dried over MgSO4 and concentrated in vacuo and recrystallized from EtOAc/hexane to give 0.17 g (46%) of a white solid as the title compound: mp 164.6-166.0° C.; 1H NMR (400 MHz, Acetone-d6) δ 8.20 (d, J=1.6 Hz, 1H), 7.97-7.95 (m, 2H), 7.59-7.52 (m, 4H), 7.42 (d, J=8.6 Hz, 1H), 2.93-2.90 (m, 2H), 2.78-2.74 (m, 2H), 2.41 (s, 3H), 2.36 (s, 3H); 13C NMR (100 MHz, Acetone-d6) δ 145.0, 138.6, 135.9, 133.3, 132.4, 130.0, 129.5, 127.9, 120.3, 119.6, 111.8, 53.5, 36.7, 25.2, 11.6; IR (diffuse reflectance) 3028, 3021, 2939, 2909, 2870, 2843, 1449, 1307, 1301, 1152, 1087, 750, 719, 692, 623 cm−1; HRMS (FAB) calcd for C18H20N2O2S+H 329.1324, found 329.1326; Anal. Calcd for C18H20N2O2S: C, 65.83; H, 6.14; N, 8.53. Found: C, 65.47; H, 6.21; N, 8.38.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6.5 hours
  3. customquenched with water (12.0 mL) and 15% NaOH (12.0 mL)
  4. filtrationThe mixture was filtered through diatomaceous earth
  5. concentrationthe filtrate was concentrated in vacuo
  6. extractionThe residue was extracted with CH2Cl2
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customrecrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-9c7b72dfc5dd44669aae151e6fe0a2d7
Source dataset
uspto-grants-2003_05
Patent number
US06565829B2

Reaction notes

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