3-Chlorophenol → (2S,4S)-4-(3-chloro-phenoxymethyl)-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

HRID 1442975Notes

Reaction equation

HRID 1442975 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH2:13][OH:14])[CH2:10][CH:9]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:41][C:42]1[CH:43]=[C:44](O)[CH:45]=[CH:46][CH:47]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][O:14][C:46]2[CH:45]=[CH:44][CH:43]=[C:42]([Cl:41])[CH:47]=2)[CH2:10][C@H:9]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 79333-ChlorophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 189679154-Hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

Product 1

HCID 59166773(2S,4S)-4-(3-chloro-phenoxymethyl)-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl esterYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester (Preparation 45, 132 mg, 0.44 mmol), triphenylphosphine (172 mg, 0.66 mmol) and 3-chlorophenol (0.069 ml, 0.66 mmol) in tetrahydrofuran (5 ml) at 0° C. under a nitrogen atmosphere was added diisopropylazodicarboxylate (0.129 ml; 0.66 mmol) dropwise and allowed to stir to room temperature over 18 hours. The solvent was removed under reduced pressure and the residue purified by chromatography on silica gel, eluting with 10% ethyl acetate/heptane to give the title compound as a colourless gum (66 mg, 37%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by chromatography on silica gel
  3. washeluting with 10% ethyl acetate/heptane

Sources & evidence

ORD record
ord-63ef6cac019b4eb5aa1d1b6c0723f38a
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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