Aluminium lithium hydride → HCID 66762969, compound

HRID 573775Notes

Reaction equation

HRID 573775 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]([C:24]([C:26]3[CH:36]=[CH:35][C:29]([C:30](OCC)=[O:31])=[CH:28][CH:27]=3)=[O:25])=[C:11]([C:37]3[CH2:41][CH2:40][CH2:39][CH:38]=3)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]([C@H:24]([C:26]3[CH:27]=[CH:28][C:29]([CH2:30][OH:31])=[CH:35][CH:36]=3)[OH:25])=[C:11]([C:37]3[CH2:41][CH2:40][CH2:39][CH:38]=3)[C:10]1=2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68061458HCID 68061458, compound

Product 1

HCID 66762969HCID 66762969, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

410 mg (S)-ethyl 4-(5-(tert-butyldimethylsilyloxy)-4-cyclopentenyl-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbonyl)benzoate are dissolved in 5 ml tetrahydrofurane and treated dropwise with 1.5 ml of a 1 M solution of lithiumaluminium hydride in tetrahydrofurane. The mixture is stirred for 8 hours at room temperature, cooled to 0° C. and the reaction is quenched by careful addition of 130 μl water and 130 μl of 4 M aqueous sodium hydroxide. After diluting with ethylacetate the mixture is dried with magnesium sulphate and filtered. The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethylacetate 100:0 to 60:40).

Workup

  1. temperaturecooled to 0° C.
  2. customthe reaction is quenched by careful addition of 130 μl water and 130 μl of 4 M aqueous sodium hydroxide
  3. additionAfter diluting with ethylacetate the mixture
  4. dry with materialis dried with magnesium sulphate
  5. filtrationfiltered
  6. customThe solvents are evaporated in vacuo
  7. customthe residue is chromatographed on silica gel (cyclohexane/ethylacetate 100:0 to 60:40)

Sources & evidence

ORD record
ord-7ba0a6afb93a42609be30b2185248be7
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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