Water → HCID 22676823, compound

HRID 1006262Notes

Reaction equation

HRID 1006262 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH:20]=[O:21])[CH:18]=3)[N:13]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=3)[C:12]=2[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>C(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][OH:21])[CH:18]=3)[N:13]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=3)[C:12]=2[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22676835HCID 22676835, compound

Product 1

HCID 22676823HCID 22676823, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 3-(4-tert-butylphenyl)-5-formyl-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 140, 700 mg, 1.493 mmol) was dissolved in ethanol (15 mL) and cooled to 0° C. Sodium borohydride (57 mg, 1.50 mmol) was added, and the solution was stirred for 1 hour. Water (27 μL, 1.5 mmol) was added, and the mixture was allowed to warm to room temperature. The mixture was concentrated via rotary evaporation, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate, and concentrated. The resulting crude oil was purified by flash chromatography on silica gel eluted with hexane then 20% ethyl acetate/hexane. The title compound was collected as a foam (530 mg, 75%). The product had: 1H NMR (300 MHz, acetone-d6) δ 7.56-7.55 (m, 1 H), 7.53-7.51 (m, 1 H), 7.50-7.47 (m, 2 H), 7.41-7.39 (m, 1 H), 7.37-7.34 (m, 2 H), 7.18-7.16 (m, 1 H), 6.77-6.75 (m, 1 H), 6.68-6.70 (m, 2 H), 5.85 (s, 2 H), 4.65 (d, 2 H), 4.09 (q, 2 H), 4.06-4.04 (m, 1 H), 3.70 (s, 3 H), 1.38 (s, 9 H), 0.96 (t, 3 H); mass spectroscopy gave MH+=472.2 (calc'd exact mass for C30H33NO4=471.24).

Workup

  1. temperatureto warm to room temperature
  2. concentrationThe mixture was concentrated via rotary evaporation
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe resulting crude oil was purified by flash chromatography on silica gel
  9. washeluted with hexane
  10. customThe title compound was collected as a foam (530 mg, 75%)
  11. custommass spectroscopy gave MH+=472.2 (calc'd exact mass for C30H33NO4=471.24)

Sources & evidence

ORD record
ord-7f1651664a184ef0bfc732d24f700691
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

Loading…