Hexane → HCID 20664170, compound

HRID 1068205Notes

Reaction equation

HRID 1068205 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C@@H:28]1[C@@H:32]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)[CH2:31][N:30]([C@@H:40]2[C:44]([CH3:46])([CH3:45])[CH2:43][O:42][C:41]2=[O:47])[CH2:29]1)(C(C)(C)C)(C)C.CCCCCC.C(OCC)(=O)C>C1COCC1.C(OCC)C>[OH:26][CH2:27][C@@H:28]1[C@@H:32]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)[CH2:31][N:30]([C@@H:40]2[C:44]([CH3:45])([CH3:46])[CH2:43][O:42][C:41]2=[O:47])[CH2:29]1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 20664171HCID 20664171, compound

Product 1

HCID 20664170HCID 20664170, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (3.6 mL, 1N in THF, 3.6 mmol) was added to a solution of dihydro-3-(R)-(3-(R)-((t-butyldimethylsilyloxy)methyl)-4-(S)-(3-fluorophenyl)-pyrrolidin-1-yl)-4,4-dimethyl-2(3H)furanone (500 mg, 1.2 mmol, from Step A) in 1 mL of THF. After 2 h. at room temperature, the solution was diluted with diethyl ether and washed with 1N NaOH and brine. The solution was dried over Na2SO4, filtered and concentrated. Flash chromatography (1:1 hexane:ethyl acetate) provided 203 mg (55% yield) of the title compound. 1H NMR (300 MHz, CDCl3). δ1.17 (s, 3H), 1.22 (s, 3H), 1.80-1.90 (m, 1H), 2.39-2.52 (m, 1H), 3.03-3.20 (m, 5H), 3.25-3.32 (m, 1H), 3.58-3.67 (m, 1H), 3.69-3.78 (m, 1H), 3.88-3.98 (m, 2H), 6.85-6.95 (m, 1H), 7.00-7.10 (m, 2H), 7.21-7.32 (m, 1H). ESI-MS. M/z; (M+H)=308.2.

Workup

  1. washwashed with 1N NaOH and brine
  2. dry with materialThe solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0aa883e4b88e488582576aaa7eb75d69
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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