Water → HCID 59129406, compound

HRID 1964333Notes

Reaction equation

HRID 1964333 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([C:9]1[N:10]([CH2:21][CH2:22][OH:23])[C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=2)([CH3:8])[CH3:7])C.CC(C[AlH]CC(C)C)C.O>C1COCC1>[OH:23][CH2:22][CH2:21][N:10]1[C:11]2[C:16](=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][CH:12]=2)[CH:17]=[C:9]1[C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][OH:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 59129375HCID 59129375, compound

Product 1

HCID 59129406HCID 59129406, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[1-(2-hydroxy-ethyl)-5-nitro-1H-indol-2-yl]-3-methyl-butyric acid ethyl ester (700 mg, 2.1 mmol) in THF (25 mL) was added DIBAL-H (1.0 M, 4.2 mL, 4.2 mmol) at −78° C. The mixture was stirred at room temperature for 1 h. Water (2 mL) was added and the resulting mixture was extracted with EtOAc (15 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by chromatography on silica gel (15% ethyl acetate/petroleum) to afford 3[1-(2-hydroxy-ethyl)-5-nitro-1H-indol-2-yl]-3-methyl-butan-1-ol (300 mg, 49%). 1H NMR (300 MHz, d-DMSO) δ 8.42 (d, J=1.5 Hz, 1 H), 7.95 (dd, J=1.2, 8.7 Hz, 1 H), 6.36 (d, J=9.3 Hz, 1 H), 6.50 (s, 1 H), 5.25 (br s, 1 H), 4.46-4.42 (m, 4 H), 3.69-3.66 (m, 2 H), 3.24-3.21 (m, 2 H), 1.42 (s, 6 H).

Workup

  1. extractionthe resulting mixture was extracted with EtOAc (15 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. customevaporated under vacuum
  4. customThe residue was purified by chromatography on silica gel (15% ethyl acetate/petroleum)

Sources & evidence

ORD record
ord-27d2e116f95541cd9b23e812577c22cd
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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