Tetrahydrofuran → HCID 42604334, compound

HRID 517387Notes

Reaction equation

HRID 517387 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].C[C:29]([CH3:32])([O-:31])[CH3:30].[K+].[C:34]1([CH2:40][CH2:41][C@H:42]([O:61][CH:62]2[CH2:67][CH2:66][CH2:65][CH2:64][O:63]2)[CH2:43][CH2:44][C@@H:45]2[C@@H]3[C@@H](OC(O)C3)C[C@H:46]2[O:54][CH:55]2[CH2:60][CH2:59][CH2:58][CH2:57][O:56]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Cl-].[NH4+].[CH2:70]1COC[CH2:71]1>>[OH:31][C@@H:29]1[C@H:30]([CH2:70]/[CH:71]=[CH:8]\[CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])[C@@H:45]([CH2:44][CH2:43][C@@H:42]([O:61][CH:62]2[CH2:67][CH2:66][CH2:65][CH2:64][O:63]2)[CH2:41][CH2:40][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C@H:46]([O:54][CH:55]2[CH2:60][CH2:59][CH2:58][CH2:57][O:56]2)[CH2:32]1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 42604333HCID 42604333, compound

Product 1

HCID 42604334HCID 42604334, compound

Conditions

Temperature
-20 °C

Procedure

A suspension of (4-carboxybutyl)triphenylphosphonium bromide (84.0 g, 189.5 mmol) and potassium tert-butoxide (44.0 g, 392.1 mmol) in THF (700 mL) was cooled to −20° C. for 30 min. A solution of (3aR,4R,5R,6aS)-4-((3R)-5-phenyl-3-((tetrahydro-2H-pyran-2-yl)oxy)pentyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol (30 g from Example 25) in THF (50 mL) at −20° C. was added and the reaction mixture was stirred for 16 hr. Then saturated aqueous solution of ammonium chloride (500 mL) was added and the resulting suspension was stirred for 30 min at room temperature. After separation of the organic layers, the aqueous layer was adjusted to have a pH of 6.0 by addition of a 2M sodium bisulfate solution and extracted with ethyl acetate (300 mL). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure to give 54.0 g of crude title compound.

Workup

  1. stirringthe resulting suspension was stirred for 30 min at room temperature
  2. customAfter separation of the organic layers
  3. additionby addition of a 2M sodium bisulfate solution
  4. extractionextracted with ethyl acetate (300 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc91b5cd49844f40acb6343475f45a20
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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