Tetrahydrofuran → HCID 12132433, compound

HRID 2307400Notes

Reaction equation

HRID 2307400 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[NH:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[CH2:17]O.C1(P([C:32]2[CH:37]=[CH:36]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC[O:40][C:41](/N=N/C(OCC)=O)=[O:42].[CH2:50]1COCC1>>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH2:17][C@@H:13]1[CH2:14][CH2:15][CH2:16][N:12]1[C:41]([O:42][C:37]([CH3:36])([CH3:32])[CH3:50])=[O:40]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 795792-Methyl-3-nitrophenolHCID 90908ProlinolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 12132433HCID 12132433, compoundYield 91%

Procedure

A stirred solution of 2-methyl-3-nitrophenol (3.80 g, 24.84 mmol), (S)-(−)-1-tert-butoxycarbonyl)-2-pyrrolidinemethanol (5.0 g, 24.8 mmol) and triphenylphosphine (6.5 g, 24.8 mmol) in THF is treated with diethylazodicarboxylate (4.3 g, 24.8 mmol), stirred for 3 h at room temperature and concentrated in vacuo. The resultant residue is mixed with ether, stored at 0° C. overnight and filtered. The filtrate is concentrated in vacuo to give a residue which is purified by chromatography (silica gel, EtOAc:hexanes, 20:80) to afford the title compound as a light yellow semisolid, 7.73 g, (91% yield), identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe resultant residue is mixed with ether
  3. waitstored at 0° C. overnight
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  6. customto give a residue which
  7. customis purified by chromatography (silica gel, EtOAc:hexanes, 20:80)

Sources & evidence

ORD record
ord-1a18eab0fbee412cb579dbb55719af2f
Source dataset
uspto-grants-2004_12
Patent number
US06831094B2

Reaction notes

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