Diethyl Ether → (1-(pyrrolidin-1-ylmethyl)cyclopropyl)methanol

HRID 1406431Notes

Reaction equation

HRID 1406431 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1([C:14]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=O)[CH2:13][CH2:12]1)=O.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].C(OCC)C>C1COCC1>[N:16]1([CH2:14][C:11]2([CH2:9][OH:8])[CH2:13][CH2:12]2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 66854469HCID 66854469, compound

Product 1

HCID 66854227(1-(pyrrolidin-1-ylmethyl)cyclopropyl)methanolYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminium hydride solution (20 mL, 1M) in THF was added slowly to a solution of 1-(pyrrolidine-1-carbonyl)-cyclopropanecarboxylic acid methyl ester (2.2 g, 11 mmol) in THF at 0° C. (ice/water), under a nitrogen atmosphere, and the resulting solution stirred for ˜3 hrs at room temperature. The solution was cooled, 0° C. (ice/water), and sodium sulphate decahydrate (4.9 g, 15 mmol) was added portion-wise to give a white suspension. Diethyl ether (25 mL) was added and the suspension stirred for ˜18 hrs. at room temperature. The resulting suspension was filtered, through celite, and the solids washed with diethyl ether (2×50 mL). The combined filtrates were concentrated to give (1-pyrrolidin-1-ylmethyl-cyclopropyl)-methanol as a pale yellow oil 1.45 g, 84%.

Workup

  1. additionwas added portion-wise
  2. customto give a white suspension
  3. stirringthe suspension stirred for ˜18 hrs
  4. customat room temperature
  5. filtrationThe resulting suspension was filtered, through celite
  6. washthe solids washed with diethyl ether (2×50 mL)
  7. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-d33b990bb9754b51ac7f3587e962a976
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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