Triphenylphosphine → HCID 66703997, compound

HRID 424437Notes

Reaction equation

HRID 424437 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]2[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]2)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:54][CH2:55][CH2:56][CH2:57]O>O1CCCC1>[Br:54][CH2:55][CH2:56][CH2:57][O:15][C:16]1[CH:21]=[CH:20][C:19]([C@@H:22]2[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66703958HCID 66703958, compound

Product 1

HCID 66703997HCID 66703997, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (40% in toluene, 13.6 g, 26.9 mmol) was added to a solution of tert-butyl (2S)-2-(4-hydroxyphenyl)morpholine-4-carboxylate (5.0 g, 17.9 mmol), triphenylphosphine (7.1 g, 27.1 mmol) and 3-bromopropanol (3.75 g, 27.0 mmol) in tetrahydrofuran (100 ml) and the solution was stirred for 10 hours at room temperature. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting 5-10% methanol in chloroform to furnish tert-butyl (2S)-2-(4-(3-bromopropyloxy)phenyl)morpholine-4-carboxylate (7.16 g, 100%) as a colorless oil.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting 5-10% methanol in chloroform

Sources & evidence

ORD record
ord-13042097aeaa4f78b0f7a3aff50d842f
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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