Sodium borohydride → HCID 178448421, compound

HRID 1028178Notes

Reaction equation

HRID 1028178 reaction equation
[CH2:1]([N:5]1[C:9]2[CH2:10][O:11][CH2:12][C:13](=[O:14])[C:8]=2[S:7]/[C:6]/1=[N:15]\[C:16](=[O:26])[C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[O:24][CH3:25])[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>O1CCCC1>[CH2:1]([N:5]1[C:9]2[CH2:10][O:11][CH2:12][CH:13]([OH:14])[C:8]=2[S:7]/[C:6]/1=[N:15]\[C:16](=[O:26])[C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[O:24][CH3:25])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178448420HCID 178448420, compound

Product 1

HCID 178448421HCID 178448421, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 10 (50 mg, 0.13 mmol) in tetrahydrofuran (5 mL) was added sodium borohydride (5.8 mg, 0.15 mmol, Aldrich). The reaction mixture was stirred at room temperature for 6 h and then quenched with saturated aqueous NH4Cl solution. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280 ™ (SiO2, 0-5% methanol in methylene chloride) to afford 20 mg (40%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.93 (t, J=7.3 Hz, 3H), 1.24-1.45 (m, 2H), 1.59-1.77 (m, 2H), 3.72 (dd, J=11.7, 4.2 Hz, 1H), 3.80 (s, 3H), 3.84-3.93 (m, 1H), 3.99-4.10 (m, J=7.1 Hz, 2H), 4.56 (d, J=5.2 Hz, 1H), 4.58-4.84 (m, 2H), 5.70 (d, J=5.9 Hz, 1H), 7.12 (d, J=8.7 Hz, 1H), 7.44-7.50 (m, 1H), 7.75 (d, J=2.8 Hz, 1H); MS (ESI+) m/z 397 (M+H)+.

Workup

  1. customquenched with saturated aqueous NH4Cl solution
  2. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b6c3f99d508b4455aea0e1c04f569520
Source dataset
uspto-grants-2014_05
Patent number
US08735434B2

Reaction notes

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