HCID 67490821, compound → HCID 67490975, compound

HRID 1917328Notes

Reaction equation

HRID 1917328 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:10](=[O:11])[N:9]([C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH2:8][C@H:7]1[C:20]1([CH2:23][O:24][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:22][CH2:21]1)=[O:5])[CH3:2]>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[C:10](=[O:11])[N:9]([C@H:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH2:8][C@H:7]1[C:20]1([CH2:23][OH:24])[CH2:21][CH2:22]1)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 67490821HCID 67490821, compound

Product 1

HCID 67490975HCID 67490975, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A hydrogen fluoride-pyridine complex (10 mL) was added dropwise to a solution of (3R)-3-[1-(tert-butyldiphenylsiloxymethyl)cyclopropan-1-yl]-5-oxo-1-[(1S)-1-phenylethyl]pyrrolidin-4-ylcarboxylic acid ethyl ester (2.81 g, 4.93 mmol) in pyridine (20 mL) at 0° C. over five minutes. The mixture was stirred at room temperature for 2.5 hours and then poured into ice water (150 mL), followed by extraction with ethyl acetate (300 mL). The resulting organic layer was washed with a 10% citric acid solution (100 mL), water (100 mL), and brine (100 mL) and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and then the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2→1:1→2:1) to give 1.378 g (84%) of the title compound as a pale yellow gummy solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate (300 mL)
  2. washThe resulting organic layer was washed with a 10% citric acid solution (100 mL), water (100 mL), and brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2→1:1→2:1)

Sources & evidence

ORD record
ord-aa2a952bea434c11a8a4addbe5a16ac3
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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