Potassium tert-butoxide → HCID 117842884, compound

HRID 2209199Notes

Reaction equation

HRID 2209199 reaction equation
CC(C)([O-])C.[K+].[OH:7][C@@H:8]([C@H:10]1[CH2:14][N:13]([C@@H:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH3:16])[C:12](=[O:25])[CH2:11]1)[CH3:9].Cl[C:27]1[C:28]2[N:29]([N:45]=[CH:46][C:47]=2[CH3:48])[CH:30]=[C:31]([C:33]2[CH:38]=[CH:37][C:36]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)=[CH:35][CH:34]=2)[N:32]=1>C1COCC1>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C@H:15]([N:13]2[CH2:14][C@H:10]([C@H:8]([O:7][C:27]3[C:28]4[N:29]([N:45]=[CH:46][C:47]=4[CH3:48])[CH:30]=[C:31]([C:33]4[CH:38]=[CH:37][C:36]([N:39]5[CH2:44][CH2:43][O:42][CH2:41][CH2:40]5)=[CH:35][CH:34]=4)[N:32]=3)[CH3:9])[CH2:11][C:12]2=[O:25])[CH3:16])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxide2×HCID 117843266HCID 117843266, compoundHCID 117843967(R)-4-((R)-1-hydroxyethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one2×

Product 1

HCID 117842884HCID 117842884, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of 1M potassium tertbutoxide in THF (0.10 mL, 0.10 mmol) was added to a solution of (R)-4-((R)-1-hydroxyethyl)-1-4R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 1.04 (27 mg, 0.1 mmol) in THF (0.5 mL) at room temperature. After 15 minutes, a solution of 4-(4-(4-chloro-3-methylpyrazolo[1,5-a]pyrazin-6-yl)phenyl)morpholine 5.11 (20 mg, 0.06 mmol) in THF (1.2 mL) was added under argon. After 90 minutes, an additional 14 mg of (R)-4-((R)-1-hydroxyethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 1.04 and 0.05 mL of 1M potassium tertbutoxide in THF were added. After 5 hours, mixture was quenched by addition of sat. NH4Cl (aq) and extracted with ethyl acetate. Combined organics were washed with 1:1 water/brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to yield (R)-1-((R)-1-(4-methoxyphenyl)ethyl)-4-((R)-1-(3-methyl-6-(4-morpholinophenyl)pyrazolo[1,5-a]pyrazin-4-yloxy)ethyl)pyrrolidin-2-one 5.12, which was used without further purification.

Workup

  1. waitAfter 90 minutes
  2. waitAfter 5 hours
  3. custommixture was quenched by addition of sat. NH4Cl (aq)
  4. extractionextracted with ethyl acetate
  5. washCombined organics were washed with 1:1 water/brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-680eeb5a46454b1085a5097331c283ff
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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