Triphenylphosphine → Tert-butyl 2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-phenylmorpholine-4-carboxylate

HRID 271998Notes

Reaction equation

HRID 271998 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11](O)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:12][N:13]([CH2:21][CH2:22][OH:23])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][CH2:10][C:11]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:23][CH2:22][CH2:21][N:13]([C:14]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:20])[CH2:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 59835972Tert-butyl 4-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-2-phenylbutyl(2-hydroxyethyl)carbamate

Product 1

HCID 59835991Tert-butyl 2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-phenylmorpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of tert-butyl 4-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-2-phenylbutyl(2-hydroxyethyl)carbamate (770 mg, 1.7 mmol) and triphenylphosphine (551 mg, 2.1 mmol) in 8 mL toluene was added diethyl azodicarboxylate (0.96 mL of a 40% solution in toluene, 2.1 mmol) and the reaction was stirred for 24 h. After evaporation, the residue was chromatographed (10% EtOAc/hex) to afford tert-butyl 2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-phenylmorpholine-4-carboxylate as an oil, which was used without further purification. ESI-MS 422 (M+H).

Workup

  1. customAfter evaporation
  2. customthe residue was chromatographed (10% EtOAc/hex)

Sources & evidence

ORD record
ord-d1e452641268416a85d5d1f36c764c68
Source dataset
uspto-grants-2008_11
Patent number
US07452992B2

Reaction notes

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