Sodium borohydride → HCID 178490701, compound

HRID 76256Notes

Reaction equation

HRID 76256 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([CH:10]=[O:11])/[C:7](=[N:12]/[C:13](=[O:23])[C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])/[S:6]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C1COCC1>[C:1]([N:5]1[CH:9]=[C:8]([CH2:10][OH:11])/[C:7](=[N:12]/[C:13](=[O:23])[C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])/[S:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178490700HCID 178490700, compound

Product 1

HCID 178490701HCID 178490701, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 21A (50 mg, 0.14 mmol) in THF (10 mL) was treated with sodium borohydride (21 mg, 0.57 mmol) at −40° C. for 1 hr, quenched with saturated NH4Cl, extracted with EtOAc (2×), dried over MgSO4, filtered and concentrated to afford 50 mg of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.67 (s, 9 H) 3.93 (s, 3 H) 4.88 (s, 2 H) 6.94 (d, J=8.85 Hz, 1 H) 7.37 (dd, J=8.85, 3.05 Hz, 1 H) 8.05 (s, 1 H) 8.08 (d, J=2.75 Hz, 1 H); MS (DCI/NH4+) m/z 355 (M+H)+.

Workup

  1. customquenched with saturated NH4Cl
  2. extractionextracted with EtOAc (2×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ffa7ef6890664982851b7101d2965c18
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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