Lithium tri-n-butoxyaluminum hydride → HCID 131722002, compound

HRID 1954032Notes

Reaction equation

HRID 1954032 reaction equation
[H-].C(O[Al](OCCCC)OCCCC)CCC.[Li+].[CH2:19]([C@@H:21]1[CH:47]=[C:46]([CH3:48])[CH2:45][C@H:44]([CH3:49])[CH2:43][C@H:42]([O:50][CH3:51])[C@H:41]2[O:52][C@:37]([OH:56])([C@H:38]([CH3:55])[CH2:39][C@@H:40]2[O:53][CH3:54])[C:36](=[O:57])[C:35](=[O:58])[N:34]2[C@@H:29]([CH2:30][CH2:31][CH2:32][CH2:33]2)[C:28](=[O:59])[O:27][C@H:26](/[C:60](/[CH3:71])=[CH:61]/[C@@H:62]2[CH2:67][CH2:66][C:65](=[O:68])[C@H:64]([O:69][CH3:70])[CH2:63]2)[C@H:25]([CH3:72])[C@@H:24]([OH:73])[CH2:23][C:22]1=[O:74])[CH3:20]>C1COCC1>[CH2:19]([C@@H:21]1[CH:47]=[C:46]([CH3:48])[CH2:45][C@H:44]([CH3:49])[CH2:43][C@H:42]([O:50][CH3:51])[C@H:41]2[O:52][C@:37]([OH:56])([C@H:38]([CH3:55])[CH2:39][C@@H:40]2[O:53][CH3:54])[C:36](=[O:57])[C:35](=[O:58])[N:34]2[C@@H:29]([CH2:30][CH2:31][CH2:32][CH2:33]2)[C:28](=[O:59])[O:27][C@H:26](/[C:60](/[CH3:71])=[CH:61]/[C@@H:62]2[CH2:67][CH2:66][C@H:65]([OH:68])[C@H:64]([O:69][CH3:70])[CH2:63]2)[C@H:25]([CH3:72])[C@@H:24]([OH:73])[CH2:23][C:22]1=[O:74])[CH3:20]

Participants

4

Reactant 2

HCID 16702147Lithium tri-n-butoxyaluminum hydrideHCID 131722001HCID 131722001, compound

Product 1

HCID 131722002HCID 131722002, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

Lithium tri-n-butoxyaluminum hydride (0.2 mL, 1M in THF) was slowly added to a stirred solution of the product from Example 15 (0.058 g) in 1 mL of anhydrous THF at -70° C. under a nitrogen atmosphere. After stirring at -70° C. for 3 hours, the mixture was partitioned between 50 mL of ether and 10 mL of 1N-HCl. The etheral solution was washed with brine, dried over magnesium sulfate anhydrous. The obtained crude product was purified by preparative TLC, using 35% acetone in hexane as a solvent to afford 0.025 g of the title compound.

Workup

  1. customthe mixture was partitioned between 50 mL of ether and 10 mL of 1N-HCl
  2. washThe etheral solution was washed with brine
  3. dry with materialdried over magnesium sulfate anhydrous
  4. customThe obtained crude product
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-14eeb752cd714c98adead4029425c9da
Source dataset
uspto-grants-2000_09
Patent number
US06121257

Reaction notes

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