Triphenylphosphine → HCID 21963144, compound

HRID 2211822Notes

Reaction equation

HRID 2211822 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[C:3]1=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[N:44]1[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]1.N(C([O-])=O)=NC([O-])=O>O1CCCC1>[C:53]([O:52][C:50]([N:47]1[CH2:48][CH2:49][N:44]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[O:1][CH:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:8]=[CH:9][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:11][CH:12]=3)[C:3]2=[O:17])[CH2:45][CH2:46]1)=[O:51])([CH3:56])([CH3:54])[CH3:55]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 11543684Tert-butyl 4-(2-hydroxyphenyl)piperazine-1-carboxylateHCID 21963156HCID 21963156, compoundHCID 51573101N-carboxylatoiminocarbamate

Product 1

HCID 21963144HCID 21963144, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 241 mg (0.983 mmol) 3-hydroxy-1-(4-trifluoromethyl-phenyl)-pyrrolidin-2-one, 15 mL dry tetrahydrofuran, 645 mg (2.45 mmol) triphenylphosphine, and 328 mg (1.18 mmol) N-(2-hydroxyphenyl)-4-t-butoxycarbonyl-piperazine. A solution of 398 mg (1.97 mmol) disopropyl azodicarboxylate in 10 mL dry tetrahydrofuran was added dropwise over 5 minutes, and the reaction stirred at room temperature overnight. The reaction was quenched with aqueous sodium bicarbonate solution, separated, and the aqueous layer extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated. The residue was chromatographed on silica using hexane/ethyl acetate as eluant to afford 320 mg (64%) of an oil.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. customThe reaction was quenched with aqueous sodium bicarbonate solution
  3. customseparated
  4. extractionthe aqueous layer extracted three times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-a1f52a8665fa4ff2a436ff2e2f708639
Source dataset
uspto-grants-2006_09
Patent number
US07101885B2

Reaction notes

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