Ethyl Acetate → HCID 86607833, compound

HRID 646676Notes

Reaction equation

HRID 646676 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([CH2:13]O)[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C1C=CC(P([N:29]=[N+:30]=[N-:31])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1.CCOC(C)=O>C1COCC1>[N:29]([CH2:13][C:9]1[CH:8]=[C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:12]=[CH:11][CH:10]=1)=[N+:30]=[N-:31]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 7162074[3-(Morpholin-4-yl)phenyl]methanol

Product 1

HCID 86607833HCID 86607833, compoundYield 141%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3-morpholin-4-ylphenyl)methanol (0.10 g, 0.52 mmol), in THF (1.0 mL) was cooled to 0° C. and DPPA (0.13 mL, 0.62 mmol) was added, followed by DBU (0.093 mL, 0.62 mmol). The solution was allowed to warm to r.t. and stirred for 12 h. The solution was poured into EtOAc (100 mL) and this was washed with H2O (50 mL) and 5% HCl(aq) (50 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give 0.16 g (>100% yield) of 4-[3-(azidomethyl)phenyl]morpholine, (TLC: UV active spot, Rf of 0.7 in 1:1 hexanes/EtOAc), which was used without further purification.

Workup

  1. washthis was washed with H2O (50 mL) and 5% HCl(aq) (50 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2374671a17c84964b3bb2a90d1dd2779
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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