Triphenylphosphine → HCID 86607616, compound

HRID 2357615Notes

Reaction equation

HRID 2357615 reaction equation
O[CH2:2][C@H:3]([N:5]([CH2:16][C@H:17]([OH:19])[CH3:18])[C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:18][C@H:17]1[O:19][CH2:2][C@@H:3]([CH3:4])[N:5]([C:6]([O:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:15])[CH2:16]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86607615HCID 86607615, compound

Product 1

HCID 86607616HCID 86607616, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of benzyl (R)-1-hydroxypropan-2-yl((R)-2-hydroxypropyl)carbamate (15.5 g, 58 mmol) in 150 mL THF stirred at 0° C. was added triphenyl phosphine (15 mL, 64 mmol) and stirred for 30 min. The mixture was further treated with diethyl azodicarboxylate (10 mL, 64 mmol) dropwise. The mixture was stirred at 0° C.—RT over 15 h. The mixture was concentrated in vacuo, then was treated with 4:1 hexane/ether 300 mL to precipitate the triphenylphosine oxide. The mixture was filtrated and washed with 4:1 hexane/ether 100 mL. The liquid was concentrated and purified by silica gel chromatography eluting with 20% ethyl acetate/hexane to give (2R,5R)-benzyl 2,5-dimethylmorpholine-4-carboxylate as a colorless oil.

Workup

  1. stirringstirred for 30 min
  2. stirringThe mixture was stirred at 0° C.—RT over 15 h
  3. concentrationThe mixture was concentrated in vacuo
  4. additionwas treated with 4:1 hexane/ether 300 mL
  5. customto precipitate the triphenylphosine oxide
  6. filtrationThe mixture was filtrated
  7. washwashed with 4:1 hexane/ether 100 mL
  8. concentrationThe liquid was concentrated
  9. custompurified by silica gel chromatography
  10. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ed2663b7bf9d4b36932e1fd541e42ac0
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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