Triphenylphosphine → 2-Benzyl-morpholine-4-carboxylic acid tert-butyl ester

HRID 737102Notes

Reaction equation

HRID 737102 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:18][CH2:19][OH:20])[CH2:8][CH:9](O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:7]1[CH2:18][CH2:19][O:20][CH:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8]1)=[O:21])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 57849611(2-Hydroxy-ethyl)-(2-hydroxy-3-phenyl-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 578496572-Benzyl-morpholine-4-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The above compound could be made in the following manner: 1 eq. of (2-Hydroxy-ethyl)-(2-hydroxy-3-phenyl-propyl)-carbamic acid tert-butyl ester and 1.2 eq. of triphenylphosphine could be dissolved in toluene. 1.2 eq. of diethylazodicarboxylate in toluene could be added dropwise to the resulting solution at room temperature under argon atmosphere and the mixture could be stirred overnight. The solvent could be removed in vacuo and the material purified by column chromatography.

Workup

  1. customThe solvent could be removed in vacuo
  2. customthe material purified by column chromatography

Sources & evidence

ORD record
ord-7e31a88698374e70b9d05d0e12d9f308
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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