Water → HCID 60063737, compound

HRID 2415247Notes

Reaction equation

HRID 2415247 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.F[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1.O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 643448(S)-(-)-N-Boc-prolinolHCID 178418339Butyllithium

Product 1

HCID 60063737HCID 60063737, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (Aldrich, 2.01 g, 10 mmol) in tetrahydrofura n (15 mL) at —78° C., n-BuLi (2.5 M in hexanes, 11 mmol, 4.4 mL) was added dropwise. After the addition, 4-fluoro nitrobenzene (1.41 g, 10 mmol) was added and the solution was gradually warmed to room temperature and stirred for 2 hours. The solution was poured into water and the mixture was extracted with ether. The extract was dried (Na2SO4) and concentrated to give the crude which was chromatographed (20% ethyl acetate/hexanes) to yield a pale yellow oil. 1.34 g.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ether
  3. dry with materialThe extract was dried (Na2SO4)
  4. concentrationconcentrated
  5. customto give the crude which
  6. customwas chromatographed (20% ethyl acetate/hexanes)
  7. customto yield a pale yellow oil

Sources & evidence

ORD record
ord-61f2f951b9bf40c991af7b3e62b03977
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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