Sodium hydride → HCID 23369980, compound

HRID 2221075Notes

Reaction equation

HRID 2221075 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22]Cl)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2=[O:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 233699784-(5-Chloro-pentanoylamino)-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 23369980HCID 23369980, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(5-Chloro-pentanoylamino)-piperidine-1-carboxylic acid benzyl ester (15.6 g) was added to a suspension of sodium hydride (2.12 g) in tetrahydrofuran (175 mL). After being stirred overnight, the reaction was quenched with water, then the tetrahydrofuran was removed under reduced pressure. The aqueous solution was diluted with water and extracted with methylene chloride (4×50 mL). The organic extracts were dried and evaporated to give the title compound (15 g). Rf=0.30 in ethyl acetate. MS: m/z=317 (M+H).

Workup

  1. customthe reaction was quenched with water
  2. customthe tetrahydrofuran was removed under reduced pressure
  3. additionThe aqueous solution was diluted with water
  4. extractionextracted with methylene chloride (4×50 mL)
  5. customThe organic extracts were dried
  6. customevaporated

Sources & evidence

ORD record
ord-51c6e232feac4beea4414fbd8faa7030
Source dataset
uspto-grants-2008_05
Patent number
US07368461B2

Reaction notes

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