Water → 2-[1-(Diphenylmethyl)azetidin-3-yl]ethan-1-ol

HRID 1091286Notes

Reaction equation

HRID 1091286 reaction equation
[Li].C([O:4][C:5](=O)[CH:6]=[C:7]1[CH2:10][N:9]([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8]1)C.O.[OH-].[Na+]>O1CCCC1>[CH:11]([N:9]1[CH2:10][CH:7]([CH2:6][CH2:5][OH:4])[CH2:8]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 3028194LithiumHCID 53428664Ethyl [1-(diphenylmethyl)azetidin-3-ylidene]acetate

Product 1

HCID 534408902-[1-(Diphenylmethyl)azetidin-3-yl]ethan-1-olYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminumhydride (889 mg, 23.4 mmol) was suspended in tetrahydrofuran (50 mL), and under a nitrogen stream, a tetrahydrofuran (30 mL) solution of (1-benzhydrylazetidin-3-ylidene)acetic acid ethyl ester (2.40 g, 7.81 mmol) was added dropwise over 20 minutes at 0° C. with stirring. The reaction liquor was stirred for two hours at the same temperature, and then while cooling the reaction liquor in ice, water (889 μl), 1 N sodium hydroxide (889 μl) and water (8.57 mL) were added in this order. The resulting mixture was dried over anhydrous sodium sulfate. The insoluble was separated by filtration, and the mother liquor was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 40M, ethyl acetate:n-hexane=1:1 to ethyl acetate), to obtain the title compound (1.58 g, 76%) as an oily matter.

Workup

  1. stirringThe reaction liquor was stirred for two hours at the same temperature
  2. temperaturewhile cooling the reaction liquor in ice
  3. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
  4. customThe insoluble was separated by filtration
  5. concentrationthe mother liquor was concentrated under reduced pressure
  6. customThe obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 40M, ethyl acetate:n-hexane=1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-8a366174f1ef4939bfdc9cf244f2fffa
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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