Sodium borohydride → HCID 178518420, compound

HRID 751541Notes

Reaction equation

HRID 751541 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[C:3]=1[C:11]1[C:12](=[O:33])[NH:13][C:14](=[O:32])[C:15]=1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH:25]2[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]2)[CH:17]=1.[BH4-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[C:3]=1[C:11]1[C:12](=[O:33])[NH:13][C:14](=[O:32])[C:15]=1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([C@H:25]2[CH2:26][CH2:27][C@@H:28]([OH:31])[CH2:29][CH2:30]2)[CH:17]=1.[F:1][C:2]1[CH:10]=[CH:9][C:5]2[CH:6]=[CH:7][O:8][C:4]=2[C:3]=1[C:11]1[C:12](=[O:33])[NH:13][C:14](=[O:32])[C:15]=1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([C@H:25]2[CH2:26][CH2:27][C@H:28]([OH:31])[CH2:29][CH2:30]2)[CH:17]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 69269364HCID 69269364, compound

Product 2

HCID 178518420HCID 178518420, compoundHCID 178518421HCID 178518421, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool a solution of 3-(6-fluorobenzofur-7-yl)-4-[1-(4-oxocyclohexyl)-1H-indol-3-yl]pyrrole-2,5-dione (395 mg, 0.89 mmol) in tetrahydrofuran (20 ml) in an ice bath. Add sodium borohydride (10 mg, 0.27 mmol) in one portion and stir for 5 minutes. Add another portion of sodium borohydride (10 mg, 0.27 mmol) and stir for 10 minutes in the ice bath. Quench the reaction is with water, then dilute with ethyl acetate, wash with water, 1N HCl, brine, dry over magnesium sulfate, filter, concentrate to a red foam. Purification by flash chromatography separates cis and trans isomers to give cis 3-(6-fluorobenzofur-7-yl)-4-[1-(4-hydroxycyclohexyl)-1H-indol-3-yl]pyrrole-2,5-dione and trans 3-(6-fluorobenzofur-7-yl)-4-[1-(4-hydroxycyclohexyl)-1H-indol-3-yl]pyrrole-2,5-dione as red solids. ES(M++H): 445.1.

Workup

  1. customQuench the reaction
  2. additiondilute with ethyl acetate
  3. washwash with water, 1N HCl, brine
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate to a red foam
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-8d0c695c2c7f46859efc40c114d0e48b
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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