Sodium borohydride → HCID 86744042, compound

HRID 2108106Notes

Reaction equation

HRID 2108106 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:8][CH2:7]2)[O:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:12][C:3]1=2.[BH4-].[Na+]>C(Cl)Cl.CO>[OH:1][CH:2]1[C:6]2([CH2:7][CH2:8]2)[O:5][C:4]2[CH:9]=[CH:10][C:11]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][C:22]4[CH:23]=[C:24]([O:32][CH3:33])[C:25]([O:30][CH3:31])=[C:26]([O:28][CH3:29])[CH:27]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:12][C:3]1=2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 14849708HCID 14849708, compound

Product 1

HCID 86744042HCID 86744042, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a mixture of methylene chloride (2 ml) and methanol (10 ml) is dissolved 1-[3-oxospiro[benzofuran-2(3H), 1'-cyclopropan]-5-ylcarbonyl]-4-(3,4,5-trimethoxybenzyl)piperazine (0.5 g). To the solution is added, while stirring under ice-cooling, sodium borohydride (0.2 g). The reaction mixture is concentrated under reduced pressure. After addition of water (50 ml), the residue is extracted with ethyl acetate. The extract is washed with water, dried, and concentrated to give 1-[3-hydroxyspiro[benzofuran-2(3H), 1'-cyclopropan]-5-ylcarbonyl]-4-(3,4,5-trimethoxybenzyl)piperazine (0.48 g) as a colorless oily product. This product (0.15 g) and fumaric acid (0.04 g) are dissolved in methanol (3 ml). The mixture is concentrated under reduced pressure. To the concentrate is added ether to give 1-[3-hydroxyspiro[benzofuran-2(3H), 1'-cyclopropan]-5-ylcarbonyl]-4-(3,4,5-trimethoxybenzyl)piperazine-fumarate (0.13 g) as a powdery product.

Workup

  1. additionTo the solution is added
  2. temperaturecooling
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. additionAfter addition of water (50 ml)
  5. extractionthe residue is extracted with ethyl acetate
  6. washThe extract is washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f4a55b39f8f34a65beff0d9155056c83
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

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