Sodium borohydride → HCID 178515596, compound

HRID 2235269Notes

Reaction equation

HRID 2235269 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[C:6]1=[O:17].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:11][CH2:12][C@H:13]([OH:16])[CH2:14][CH2:15]2)[C:6]1=[O:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11624255HCID 11624255, compound

Product 1

HCID 178515596HCID 178515596, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3-(2,4-dichloro-benzyl)-1-(4-oxo-cyclohexyl)-pyrrolidin-2-one (Example 14) (6.19 g, 18.19 mmol) in MeOH (200 mL) and cool to 0° C. under nitrogen. Add sodium borohydride (1.38 g, 36.39 mmol) and stir the solution at 0° C. for 4 hours. Add water (200 mL) and extract the aqueous layer with ethyl acetate (3×300 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 50-80% EtOAc-Hexane) to give 5.49 g (88%) of the title product as a white solid. 1H NMR (CDCl3) δ 7.37 (d, 1H), 7.22 (d, 1H), 7.17 (dd, 1H), 3.91-4.00 (m, 1H), 3.52-3.62 (m, 1H), 3.27-3.36 (m, 1H), 3.12-3.21 (m, 2H), 2.73-2.82 (m, 2H), 1.98-2.07 (m, 3H), 1.56-1.77 (m, 4H), 1.38-1.54 (m, 4H).

Workup

  1. extractionAdd water (200 mL) and extract the aqueous layer with ethyl acetate (3×300 mL)
  2. dry with materialCombine the organic layers and dry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify by flash column chromatography (silica gel, 50-80% EtOAc-Hexane)

Sources & evidence

ORD record
ord-bca7c0ad6c604d4e8e2f53ece3196b79
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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