3,4-dihydro-2H-pyran → HCID 57857047, compound

HRID 561764Notes

Reaction equation

HRID 561764 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[C@@H:24]([F:25])[CH2:23][C@H:22]([OH:26])[C@@H:21]1[CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:39]1[CH:44]=[CH:43][CH2:42][CH2:41][CH2:40]1>C(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Si:1]([O:18][CH2:19][C@H:20]1[C@@H:24]([F:25])[CH2:23][C@H:22]([O:26][CH:40]2[CH2:41][CH2:42][CH2:43][CH2:44][O:39]2)[C@@H:21]1[CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 57857026HCID 57857026, compound

Product 1

HCID 57857047HCID 57857047, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution consisting of (Z)-isopropyl 7-((1R,2S,3S,5S)-2-((tert-butyldiphenylsilyloxy)methyl)-3-fluoro-5-hydroxycyclopentyl)hept-5-enoate (prepared in Step D, 28.6 g, 52.8 mmol) in anhydrous DCM (500 mL) was added dihydropyran (6.69 g, 79.3 mmol). The reaction mixture was cooled to 0° C. and p-toluenesulfonic acid (25 mg) was subsequently added and the reaction was stirred for 2 hours at 0° C. The reaction mixture was then allowed to warm to room temperature and stirring was continued for another 2 hours. The crude reaction mixture was transferred to a separatory funnel, washed with saturated aqueous sodium bicarbonate solution and then with brine. The organic phase was dried over sodium sulfate, filtered, and the solvents were removed by evaporation to afford the crude title intermediate (32.7 g). The crude intermediate was carried on with no further purification.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirring
  3. waitwas continued for another 2 hours
  4. customThe crude reaction mixture
  5. customwas transferred to a separatory funnel
  6. washwashed with saturated aqueous sodium bicarbonate solution
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvents were removed by evaporation

Sources & evidence

ORD record
ord-d60972de65374a2190fb57336519115f
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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