Tetrahydrofuran → HCID 70122032, compound

HRID 2399750Notes

Reaction equation

HRID 2399750 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]([NH:26][CH2:27][CH:28]2[CH2:30][CH:29]2[C:31](OCC)=O)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1C[O:39]CC1>>[C:7]1([C:13]([NH:26][CH2:27][CH:28]2[CH2:30][C:29]2([CH3:31])[OH:39])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 19384382HCID 19384382, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 70122032HCID 70122032, compound

Procedure

To a mixture of lithium aluminum hydride (0.077 g; 2.04 mmol) in 10 ml THF is added ethyl 2-triphenylmethylaminomethylcyclopropane-1-carboxylate (0.714 g; 1.85 mmol) in 20 ml THF and stirred overnight. The reaction mixture is quenched with water, filtered, concentrated in vacuo and flash chromatographed using hexane:ethylacetate;3:l to obtain 2-triphenylmethylaminomethyl-1-hydroxy-methylcyclopropane as a clear oil which is used directly in the next step.

Workup

  1. customThe reaction mixture is quenched with water
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo and flash
  4. customchromatographed

Sources & evidence

ORD record
ord-92e8b443729b48a8b509d21aed7a8c13
Source dataset
uspto-grants-1995_09
Patent number
US05451596

Reaction notes

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