Ethyl Acetate → (1-benzhydrylazetidin-2-yl)methanol

HRID 2050193Notes

Reaction equation

HRID 2050193 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:14]2[CH2:17][CH2:16][CH:15]2[C:18](OC)=[O:19])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C>CCOCC>[C:7]1([CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:14]2[CH2:17][CH2:16][CH:15]2[CH2:18][OH:19])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 282396methyl 1-benzhydrylazetidine-2-carboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 427905(1-benzhydrylazetidin-2-yl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 0.57 g of lithium aluminium hydride in 30 ml of dry ether is dropwise added a solution of 6 g (0.021 mole) of 1-diphenylmethyl-2-methoxycarbonylazetidine [prepared in the manner described in J. Heterocyclic Chem., 6, 435 (1969) by R. M. Rodebaugh and N. H. Cromwell] in 30 ml of dry ether in a period of 15 minutes, and the mixture is stirred at room temperature for 15 minutes. The excess amount of lithium aluminium hydride is decomposed with ethyl acetate. The insoluble materials are filtered off and washed with dry ether. The combined filtrate and washings are evaporated to dryness under reduced pressure. The residue is dissolved in ether and the resulting solution is evaporated to yield 4.7 g of crude syrupy 1-diphenylmethyl-2-hydroxymethylazetidine in 90% yield.

Workup

  1. customprepared in the manner
  2. filtrationThe insoluble materials are filtered off
  3. washwashed with dry ether
  4. customThe combined filtrate and washings are evaporated to dryness under reduced pressure
  5. dissolutionThe residue is dissolved in ether
  6. customthe resulting solution is evaporated

Sources & evidence

ORD record
ord-d65407d6cf014804bd268dcc2f7d4a58
Source dataset
uspto-grants-1980_04
Patent number
US04200628

Reaction notes

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