Tetrahydrofuran → HCID 69269361, compound

HRID 751526Notes

Reaction equation

HRID 751526 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)[CH:10]([CH2:23]C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1C[O:34]CC1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)[CH:10]([CH2:23][OH:34])[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 69267751HCID 69267751, compound

Product 1

HCID 69269361HCID 69269361, compoundYield 45.2%

Procedure

Dissolve 1-(1-tert-Butoxycarbonyl-3-ethyl-piperidin-4-yl)-1H-indole (2.86 g, 7.7 mmol) in TIP (25 ml) and stir at ambient temperature. Add a 1M solution of lithium aluminum hydride in THF (8.5 ml, 8.5 mmol) dropwise via syringe. Stir for two hours, then quench with 0.34 ml water, 0.26 ml 5N sodium hydroxide, and 1.2 ml water. Filter through a pad of Celite®, concentrate to an oil. Purify by flash chromatography to yield the title compound (1.15 g, 45%). ES (M++1): 275.1

Workup

  1. stirringStir for two hours
  2. customquench with 0.34 ml water, 0.26 ml 5N sodium hydroxide, and 1.2 ml water
  3. filtrationFilter through a pad of Celite®
  4. concentrationconcentrate to an oil
  5. customPurify by flash chromatography

Sources & evidence

ORD record
ord-4ece4803ffbf40fea51bcdf117743781
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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