Tetrahydrofuran → 1,1-Dicyclopropyl-2-dibenzylamino-ethanol

HRID 1865892Notes

Reaction equation

HRID 1865892 reaction equation
[CH:1]1([Mg]Cl)[CH2:3][CH2:2]1.C(O[C:9](=[O:26])[CH2:10][N:11]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C.O1[CH2:31][CH2:30][CH2:29]C1>>[CH:1]1([C:9]([CH:29]2[CH2:30][CH2:31]2)([OH:26])[CH2:10][N:11]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 3553452Ethyl 2-(dibenzylamino)acetateHCID 178478986HCID 178478986, compound

Product 1

HCID 687982851,1-Dicyclopropyl-2-dibenzylamino-ethanolYield 26%

Procedure

To 20 ml of a 0.5 M (0.010 mol) solution of cyclopropylmagnesium chloride in tetrahydrofuran was a solution of 1.00 g (0.004 mol) dibenzylamino-acetic acid ethyl ester in 10 ml tetrahydrofuran and the mixture was allowed to stir at room temperature for 18 h. The reaction mixture was partitioned between 10% aqueous ammonium chloride and ethyl acetate the phases were separated and the organic phase was purified by chromatography on silca gel with heptane:ethyl acetate=9:1 to 4:1 to yield 0.29 g (26% Th) of the title compound as light yellow oil. MS (ISP) (M+H+)=322.3.

Workup

  1. customThe reaction mixture was partitioned between 10% aqueous ammonium chloride and ethyl acetate the phases
  2. customwere separated
  3. customthe organic phase was purified by chromatography on silca gel with heptane

Sources & evidence

ORD record
ord-8a47aefb908540319cdb6c50eca1f7c1
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

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