Water → (1-Benzhydrylazetidin-3-yl)methanol

HRID 1896158Notes

Reaction equation

HRID 1896158 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([C:18](O)=[O:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1.CC(=O)OCC>[CH:1]([N:14]1[CH2:17][CH:16]([CH2:18][OH:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 27354401-(Diphenylmethyl)azetidine-3-carboxylic acidHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2758715(1-Benzhydrylazetidin-3-yl)methanolYield 97.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Benzhydrylazetane-3-carboxylic acid (101 mg) was dissolved in THF (2 mL) and lithium aluminium hydride (27 mg) was added. The mixture was stirred overnight at RT. Water, sodium potassium tartrate solution and EA were added. The phases were separated, the org. phase was dried (Na2SO4) and evaporated off to afford 93 mg of the desired product.

Workup

  1. customThe phases were separated
  2. dry with materialphase was dried (Na2SO4)
  3. customevaporated off

Sources & evidence

ORD record
ord-4182aa1e95a44b2688b037e8742bab44
Source dataset
uspto-grants-2013_08
Patent number
US08518912B2

Reaction notes

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