Tetrahydrofuran → HCID 66833675, compound

HRID 579579Notes

Reaction equation

HRID 579579 reaction equation
C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.[CH3:34][C:35]1([CH3:42])[C:39]([CH3:41])([CH3:40])[O:38][BH:37][O:36]1.[C:43]([NH:46][C:47]([C@@H:59]1[CH2:63][CH2:62][N:61]([S:64]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=2[N+:73]([O-:75])=[O:74])(=[O:66])=[O:65])[CH2:60]1)([CH2:55][CH2:56][CH:57]=[CH2:58])[C:48]([NH:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])(=[O:45])[CH3:44]>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir]>[C:43]([NH:46][C:47]([C@@H:59]1[CH2:63][CH2:62][N:61]([S:64]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][C:68]=2[N+:73]([O-:75])=[O:74])(=[O:66])=[O:65])[CH2:60]1)([CH2:55][CH2:56][CH2:57][CH2:58][B:37]1[O:38][C:39]([CH3:41])([CH3:40])[C:35]([CH3:42])([CH3:34])[O:36]1)[C:48]([NH:50][C:51]([CH3:54])([CH3:52])[CH3:53])=[O:49])(=[O:45])[CH3:44]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 742671,2-Bis(diphenylphosphino)ethaneHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 66833035HCID 66833035, compound

Product 1

HCID 66833675HCID 66833675, compound

Reagents, catalysts & solvents 1

HCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimerCatalyst

Procedure

In a 50 mL round bottomed flask, a solution of bis(1,5-cyclooctadiene)diiridium(I) dichloride (72 mg, 0.11 mmol) and 1,2-bis(diphenylphosphino)-ethane (84 mg, 0.21 mmol) in tetrahydrofuran (10 mL, 100 mmol) was cooled to 0° C., stirred for 15 min and treated with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (450 uL, 3.1 mmol). After additional stirring for 5 min the cooling bath was removed and the reaction mixture was allowed to warm to room temperature with stirring a period of 15 min. The reaction mixture was then recooled to 0° C. and treated with a solution of 2-acetamido-N-tert-butyl-2-((R)-1-(2-nitrophenylsulfonyl)pyrrolidin-3-yl)hex-5-enamide (1.00 g, 2.08 mmol) in tetrahydrofuran (2 mL, 20 mmol) added in a dropwise manner via syringe. After stirring for 5 min at 0° C. the reaction was warmed to room temperature and stirred until the desired product was obtained in good yield. The reaction mixture was quenched by pouring the crude into a saturated solution of aqueous sodium carbonate (50 mL). The aqueous layer was extracted using ethyl acetate (3×30 mL), and the combined organic layers were washed with saturated aqueous sodium chloride (20 mL), dried over Na2SO4, filtered and concentrated to give 2-acetamido-N-tert-butyl-2-((R)-1-(2-nitrophenylsulfonyl)pyrrolidin-3-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide (1.20 g, 94.8%) as a foam. The titled compound was used without further purification. ESI MS found for C28H45N4O8BS m/z 609.5 (M+H)+; 607.5 (M−H)−.

Workup

  1. stirringAfter additional stirring for 5 min the cooling bath
  2. customwas removed
  3. stirringwith stirring a period of 15 min
  4. customwas then recooled to 0° C.
  5. additionadded in a dropwise manner via syringe
  6. stirringAfter stirring for 5 min at 0° C. the reaction
  7. temperaturewas warmed to room temperature

Sources & evidence

ORD record
ord-5296617565884991a9315aca019a897b
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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