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Triphenylphosphine → HCID 17755966, compound

HRID 491591
Notes
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Reaction equation

HRID 491591 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24]O)=[O:18])([CH3:15])([CH3:14])[CH3:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[Cl:1])=[O:18])([CH3:15])([CH3:13])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 692642-Chloro-5-nitrophenolHCID 643448(S)-(-)-N-Boc-prolinolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 17755966HCID 17755966, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 2-chloro-5-nitrophenol (5.06 g, 29.17 mmol), (S)-(−)-1-(tert-butoxycarbonyl)-2-pyrrolidinemethanol (5.87 g, 29.17 mmol), and Ph3P (7.65 g, 29.17 mmol) in 50 mL THF, cooled to −15° C., was added dropwise, over 75 min, a solution of DIAD (6.02 g, 29.75 mmol). The reaction was warmed to RT and stirred for 18 h. The reaction was concentrated to dryness. The crude residue was treated with a small mix of Et2O and hexanes and sonicated so as to triturate out bulk of impurities, which were filtered off. The filtrate was concentrated to dryness. The resulting residue was purified by silica gel column chromatography using 7% EtOAc in hexanes to elute the title compound as a thick yellow oil.

Workup

  1. additionwas added dropwise, over 75 min
  2. concentrationThe reaction was concentrated to dryness
  3. additionThe crude residue was treated with
  4. additiona small mix of Et2O and hexanes
  5. customsonicated so as
  6. customto triturate out bulk of impurities, which
  7. filtrationwere filtered off
  8. concentrationThe filtrate was concentrated to dryness
  9. customThe resulting residue was purified by silica gel column chromatography
  10. washto elute the title compound as a thick yellow oil

Sources & evidence

ORD record
ord-f3fbdbd8ec504d2a8ccd48a1a31c967a
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07531553B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes