Sodium borohydride → HCID 44211738, compound

HRID 726175Notes

Reaction equation

HRID 726175 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][O:12][C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[S:23][CH2:22][CH2:21][C:20]3=[O:25])=[O:14])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>C(O)C>[CH2:1]([N:5]1[CH2:6][CH2:7][CH:8]([CH2:11][O:12][C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[S:23][CH2:22][CH2:21][CH:20]3[OH:25])=[O:14])[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 44211737HCID 44211737, compound

Product 1

HCID 44211738HCID 44211738, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(1-Butylpiperidin-4-ylmethyl)thiochroman-4-one-8-carboxylate (0.064 g, 0.177 mmol)(Example 2-1) was dissolved in ethanol (5 ml) and treated with sodium borohydride (0.007 g, 0.186 mmol) with stirring. After 3 h, the reaction mixture was evaporated under reduced pressure and the residue partitioned between CH2Cl2 and water. The aqueous layer was then extracted with CH2Cl2 and the combined organic extracts were dried (Na2SO4) and evaporated under reduced pressure to give the title compound as a pale yellow oil which was dried in vacuo (0.060 g, 93%) and subsequently converted to the oxalate salt. m.pt 147°-148° C.

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customthe residue partitioned between CH2Cl2 and water
  3. extractionThe aqueous layer was then extracted with CH2Cl2
  4. dry with materialthe combined organic extracts were dried (Na2SO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-45d9f804815f4f46ae7d23fb4d4adad0
Source dataset
uspto-grants-1998_01
Patent number
US05708174

Reaction notes

Loading…