Triphenylphosphine → 1-(3-tert-Butyl-isoxazol-5-yl)-3-methyl-3-(tetrahydro-pyran-4-sulfonyl)-pyrrolidin-2-one

HRID 1924867Notes

Reaction equation

HRID 1924867 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:36]([C:40]1[CH:44]=[C:43]([NH:45][C:46](=[O:61])[C:47]([CH3:60])([S:51]([CH:54]2[CH2:59][CH2:58][O:57][CH2:56][CH2:55]2)(=[O:53])=[O:52])[CH2:48][CH2:49]O)[O:42][N:41]=1)([CH3:39])([CH3:38])[CH3:37]>C(Cl)Cl>[C:36]([C:40]1[CH:44]=[C:43]([N:45]2[CH2:49][CH2:48][C:47]([CH3:60])([S:51]([CH:54]3[CH2:55][CH2:56][O:57][CH2:58][CH2:59]3)(=[O:52])=[O:53])[C:46]2=[O:61])[O:42][N:41]=1)([CH3:37])([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 44609910N-(3-tert-Butyl-isoxazol-5-yl)-4-hydroxy-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-butyramide

Product 1

HCID 446099071-(3-tert-Butyl-isoxazol-5-yl)-3-methyl-3-(tetrahydro-pyran-4-sulfonyl)-pyrrolidin-2-oneYield 51.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of di-tert-butyl azodicarboxylate (0.126 g; 0.546 mmol) in methylene chloride (2.5 mL) was added triphenylphosphine (0.143 g; 0.546 mmol). The mixture was stirred 30 minutes and N-(3-tert-butyl-isoxazol-5-yl)-4-hydroxy-2-methyl-2-(tetrahydro-pyran-4-sulfonyl)-butyramide (0.212 g; 0.546 mmol) was added. After 3 hours the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using ethyl acetate and hexanes as the eluent. Removal of the volatiles from the product-rich fractions provided 0.105 g of the solid product. 1H NMR (CDCl3) δ 6.41 (s, 1H), 4.09 (m, 4H), 3.85 (m, 1H), 3.49 (m, 2H), 3.24 (m, 1H), 2.25-1.86 (m, 5H), 1.75 (s, 3H), 1.35 (s, 9H). MS (ESI): m/e 371 (M+H).

Workup

  1. customAfter 3 hours the volatiles were removed in vacuo
  2. customThe residue was purified by silica gel chromatography
  3. customRemoval of the volatiles from the product-rich fractions

Sources & evidence

ORD record
ord-7884c0a6ef3c4bbe98170ce88e9fb4ab
Source dataset
uspto-grants-2012_05
Patent number
US08178568B2

Reaction notes

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