Ammonium Chloride → HCID 178515732, compound

HRID 2235261Notes

Reaction equation

HRID 2235261 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:15][CH2:14][C@@H:13]([OH:16])[CH2:12][CH2:11]2)[C:6]1=[O:17].C(S)C.[Na].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[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

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 45051917Sodium ethanethiolHCID 178490244HCID 178490244, compound

Product 1

HCID 178515732HCID 178515732, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 3-(2-chloro-6-methoxy-benzyl)-1-(cis-4-hydroxy-cyclohexyl)-pyrrolidin-2-one (Example 57) (150 mg, 0.44 mmol) in DMF (5 mL) and purge with nitrogen. Add sodium ethane thiol (110 mg, 1.3 mmol) and heat to 120° C. for 4 hours. Cool to room temperature and pour into ammonium chloride and extract with methylene chloride, dry over sodium sulfate, filter and concentrate. Purify over silica gel (20% hexanes in ethyl acetate) to yield 90 mg (63%) of the title compound as a pale yellow solid: Mass spectrum (apci) m/z=324.1 (M+H).

Workup

  1. custompurge with nitrogen
  2. extractionextract with methylene chloride
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify over silica gel (20% hexanes in ethyl acetate)

Sources & evidence

ORD record
ord-36054c0778964a35ad1bf6966c61ee27
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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