Sodium borohydride → HCID 86671280, compound

HRID 1615091Notes

Reaction equation

HRID 1615091 reaction equation
[CH3:1][C:2]([S:24][S:25][CH3:26])([CH3:23])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([C:13](OCC)=[O:14])[N:10]=[C:9]([C:18](OCC)=[O:19])[CH:8]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>C(O)C>[CH3:23][C:2]([S:24][S:25][CH3:26])([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH2:18][OH:19])[N:10]=[C:11]([CH2:13][OH:14])[CH:12]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 86671278Diethyl 4-(4-methyl-4-(methyldisulfanyl)pentyloxy)pyridine-2,6-dicarboxylate

Product 1

HCID 86671280HCID 86671280, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of diethyl 4-(4-methyl-4-(methyldisulfanyl)pentyloxy)pyridine-2,6-dicarboxylate (5d) (270 mg, 0.672 mmol) in absolute ethanol (7.0 mL) was added calcium chloride (224 mg, 2.017 mmol) and sodium borohydride (76 mg, 2.017 mmol). The reaction was allowed to stir at ambient temperature for 90 minutes after which it was quenched with water and concentrated in vacuo to remove the ethanol. The mixture was then extracted twice with dichloromethane. The organic extracts were combined, washed with water, dried with anhydrous magnesium sulfate and filtered through celite. The filtrate was concentrated under reduced pressure and the crude material was purified by silica gel chromatography eluting with 10% methanol/dichloromethane to yield (4-(4-methyl-4-(methyldisulfanyl)pentyloxy)pyridine-2,6-diyl)dimethanol (5e) (75 mg, 35%); 1H NMR (400 Hz, CDCl3): δ 6.63 (s, 2H), 4.60 (s, 4H), 3.95 (t, 2H, J=6.2 Hz), 3.54 (bs, 2H), 2.35 (s, 3H), 1.82 (m, 2H), 1.66 (m, 2H), 1.26 (s, 6H); MS (m/z). found 340.1 (M+Na). See FIG. 5.

Workup

  1. customwas quenched with water
  2. concentrationconcentrated in vacuo
  3. customto remove the ethanol
  4. extractionThe mixture was then extracted twice with dichloromethane
  5. washwashed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered through celite
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe crude material was purified by silica gel chromatography
  10. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-dee7f74aeda647cc86c274510e08c13d
Source dataset
uspto-grants-2014_07
Patent number
US08765740B2

Reaction notes

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