Toluene → HCID 67490888, compound

HRID 1917435Notes

Reaction equation

HRID 1917435 reaction equation
[C:1]([O:5][C:6]([C@@:8]1([CH2:24]O)[CH:12]([CH2:13][OH:14])[C:11](=[O:15])[N:10]([C@@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])[CH2:9]1)=[O:7])([CH3:4])([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>O1CCCC1>[C:1]([O:5][C:6]([C@@:8]12[CH2:24][O:14][CH2:13][CH:12]1[C:11](=[O:15])[N:10]([C@@H:16]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:17])[CH2:9]2)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67490796HCID 67490796, compound

Product 1

HCID 67490888HCID 67490888, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of (3S)-3,4-bis(hydroxymethyl)-5-oxo-1-[(R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (710 mg, 2.03 mmol) and triphenylphosphine (450 mg, 2.64 mmol) in tetrahydrofuran (10 mL) was added a solution of 40% diethyl azodicarboxylate in toluene (1.06 mL, 2.33 mmol) dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 6 h. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 40% AcOEt in hexane to afford the title compound (435 mg) as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with 40% AcOEt in hexane

Sources & evidence

ORD record
ord-3a6e0051cce54d9baf18d9282a829687
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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