(4-Carboxybutyl)triphenylphosphonium bromide → HCID 57857048, compound

HRID 561762Notes

Reaction equation

HRID 561762 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[CH3:28]C(C)([O-])C.[K+].[Si:34]([O:51][CH2:52][C@@H:53]1[C@@H:60]2[C@@H:56]([O:57]C(O)[CH2:59]2)[CH2:55][C@@H:54]1[F:62])([C:47]([CH3:50])([CH3:49])[CH3:48])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.OS([O-])(=O)=O.[K+]>C1COCC1>[Si:34]([O:51][CH2:52][C@H:53]1[C@@H:54]([F:62])[CH2:55][C@H:56]([OH:57])[C@@H:60]1[CH2:59]/[CH:28]=[CH:8]\[CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])([C:47]([CH3:50])([CH3:49])[CH3:48])([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 516920Potassium bisulfateHCID 12073621HCID 12073621, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 57857048HCID 57857048, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

4-Carboxybutyltriphenylphosphonium bromide (55.81 g, 126.0 mmol) was suspended in anhydrous THF (1.5 L) and potassium t-butoxide (252 mL, 252 mmol) was added dropwise at room temperature. After the addition was complete, the orange ylide was cooled to 0° C. and (3aR,4S,5S,6aS)-4-((tert-butyldiphenylsilyloxy)methyl)-5-fluorohexahydro-2H-cyclopenta[b]furan-2-ol (prepared in Step B, 26 g, 63 mmol) as a solution in THF was added dropwise. The reaction mixture was allowed to slowly warm to room temperature overnight with stirring. The reaction was acidified with 5% KHSO4, extracted with ethyl acetate, and washed twice with brine. The crude material was dried over sodium sulfate, filtered and evaporated to an oil. The crude product was purified on silica gel, eluted with hexanes-ethyl acetate (4:1 with 0.4% acetic acid) to afford the title intermediate (30.8 g, 97%).

Workup

  1. additionAfter the addition
  2. temperatureto slowly warm to room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washwashed twice with brine
  5. dry with materialThe crude material was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to an oil
  8. customThe crude product was purified on silica gel
  9. washeluted with hexanes-ethyl acetate (4:1 with 0.4% acetic acid)

Sources & evidence

ORD record
ord-8d6e8668d4a24d0ba405ff62ee54806d
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

Loading…