Benzoyl chloride → HCID 86592436, compound

HRID 273195Notes

Reaction equation

HRID 273195 reaction equation
[CH2:1]([O:8][N:9]([CH2:12][CH:13]1[CH:17]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:16][NH:15][C:14]1=[O:22])[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1>[CH2:1]([O:8][N:9]([CH2:12][CH:13]1[CH:17]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:16][N:15]([C:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:40])[C:14]1=[O:22])[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 86592437HCID 86592437, compound

Product 1

HCID 86592436HCID 86592436, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (+/−)-(3RS,4SR)-N-benzyloxy-N-(4-butyl-2-oxopyrrolidin-3-yl-methyl)formamide (0.18 g, 0.59 mmol) in dry THF (3 mL) at −78° C. under argon was added dropwise lithium bis(trimethylsilyl)amide in THF (1 M, 0.71 mL). After 20 min, benzoyl chloride (0.077 mL, 0.89 mmol) was added dropwise and stirring continued for 2 h. The reaction was warmed up to 0° C., quenched with saturated aq. NH4Cl (10 mL) and extracted with dichloromethane (3×10 mL). The combined organic solution was dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes 1:1) to afford (+/−)-(3RS,4SR)-N-benzyloxy-N-[4-butyl-2-oxo-1-(1-phenylmethanoyl)pyrrolidin-3-yl-methyl)formamide as a white solid (0.12 g, 50%). MS(ES) m/e 409 [M+H]+.

Workup

  1. waitcontinued for 2 h
  2. customquenched with saturated aq. NH4Cl (10 mL)
  3. extractionextracted with dichloromethane (3×10 mL)
  4. dry with materialThe combined organic solution was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes 1:1)

Sources & evidence

ORD record
ord-ca43862c2dee4458be570ff448f3a6cf
Source dataset
uspto-grants-2008_11
Patent number
US07456211B2

Reaction notes

Loading…