Sodium borohydride → 5-[(1R)-2-{4-[2-(1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)-2-hydroxyethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one

HRID 2281359Notes

Reaction equation

HRID 2281359 reaction equation
[O:1]=[S:2]1(=[O:34])[C:6]2[CH:7]=[CH:8][C:9]([C:11](=[O:33])[CH2:12][N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C@@H:20]([C:22]4[CH:31]=[CH:30][C:25]5[C:26](=[O:29])[O:27][CH2:28][C:24]=5[C:23]=4[CH3:32])[OH:21])[CH2:15][CH2:14]3)=[CH:10][C:5]=2[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[O:34]=[S:2]1(=[O:1])[C:6]2[CH:7]=[CH:8][C:9]([CH:11]([OH:33])[CH2:12][N:13]3[CH2:14][CH2:15][N:16]([CH2:19][C@@H:20]([C:22]4[CH:31]=[CH:30][C:25]5[C:26](=[O:29])[O:27][CH2:28][C:24]=5[C:23]=4[CH3:32])[OH:21])[CH2:17][CH2:18]3)=[CH:10][C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1176421725-[(1R)-2-{4-[2-(1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)-2-oxoethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one

Product 1

HCID 1176419595-[(1R)-2-{4-[2-(1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)-2-hydroxyethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-[(1R)-2-{4-[2-(1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)-2-oxoethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one (56 mg, 0.12 mmol) in 3 mL MeOH was added sodium borohydride (4.4 mg, 0.12 mmol) portion wise. The reaction was allowed to stir at ambient temperature for one hour, quenched by the addition of water and then concentrated in vacuo. The crude residue was dissolved in DCM/water mixture. The aqueous layer was extracted three times with DCM (10 mL). The organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified via MPLC (10% DCM/MeOH) to afford 5-[(1R)-2-{4-[2-(1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)-2-hydroxyethyl]piperazin-1-yl}-1-hydroxyethyl]-4-methyl-2-benzofuran-1(3H)-one as a mixture of diastereomers.

Workup

  1. customquenched by the addition of water
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude residue was dissolved in DCM/water mixture
  4. extractionThe aqueous layer was extracted three times with DCM (10 mL)
  5. dry with materialThe organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified via MPLC (10% DCM/MeOH)

Sources & evidence

ORD record
ord-8768b143d5bc41a9a8ef4379da8c24a2
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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