Sodium borohydride → HCID 11044829, compound

HRID 1182506Notes

Reaction equation

HRID 1182506 reaction equation
[OH:1][NH:2][C:3](=[O:22])[CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([OH:21])[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1.[BH4-].[Na+]>CO>[OH:1][NH:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([OH:21])[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 73117393HCID 73117393, compound

Product 1

HCID 11044829HCID 11044829, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 187 (20 mg, 0.067 mmol) in methanol (670 μL) was added solid sodium borohydride (2.5 mg, 0.067 mmol). The mixture was stirred for 15 minutes and the solvent was evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was dried (MgSO4) and concentrated. Purification by flash silica gel chromatography (6% methanol in dichloromethane) afforded the title compound 188 in 46% yield (9.1 mg). 1H NMR: (300 MHz, CD3OD) δ: 7.84-7.76 (m, 4H), 7.50-7.40 (m, 3H), 4.75 (t, J=6.6 Hz, 1H), 2.05 (t, J=7.4 Hz, 2H), 1.86-1.76 (m, 2H), 1.62-1.55 (m, 2H), 1.43-1.23 (m, 6H). HRMS: (calc.) 283.1572 (M−H2O), (found) 283.1581.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by flash silica gel chromatography (6% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ed8283c931a44d4a93f8687ba52e496c
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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