Triphenylphosphine → HCID 86601371, compound

HRID 1443069Notes

Reaction equation

HRID 1443069 reaction equation
[OH:1][CH2:2][C@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1O)[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>COCCOC>[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:1][CH2:2][C@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)[CH3:17]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 667552-EthoxyphenolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1512577tert-Butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate

Product 1

HCID 86601371HCID 86601371, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirring mixture at room temperature of (S)-2-hydroxymethyl-morpholine-4-carboxylic acid, tert-butyl ester, 2-ethoxyphenol and triphenylphosphine in DME was added dropwise diisopropyl azodicarboxylate. The solution was stirred at room temperature for 24 h, concentrated (to remove most of the DME), then suspended into hexanes. The solid that formed was filtered. The filtrate was concentrated, redissolved into diethyl ether, then washed with 1 N NaOH (2×), sat. KH2PO4 and brine solutions. The organic extract was dried (MgSO4), filtered, concentrated and chromatographed (MPLC, silica gel, 20% EtOAc in hexanes) to give (S)-2-(2-ethoxy-phenoxymethyl)-morpholine-4-carboxylic acid, tert-butyl ester as a colorless oil.

Workup

  1. concentrationconcentrated (
  2. customto remove most of the DME),
  3. customThe solid that formed
  4. filtrationwas filtered
  5. concentrationThe filtrate was concentrated
  6. dissolutionredissolved into diethyl ether
  7. washwashed with 1 N NaOH (2×), sat. KH2PO4 and brine solutions
  8. extractionThe organic extract
  9. dry with materialwas dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customchromatographed (MPLC, silica gel, 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-254ef95956994d71b89fb908439a1f75
Source dataset
uspto-grants-2010_02
Patent number
US07659394B2

Reaction notes

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