Benzoic Acid → HCID 59556039, compound

HRID 1173280Notes

Reaction equation

HRID 1173280 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:4]([CH3:14])[CH2:3]1.[C:15](O)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[C:15]([O:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:4]([CH3:14])[CH2:3]1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11008972(2S,4R)-4-hydroxy-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59556039HCID 59556039, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the alcohol of step A (0.81 g, 4.0 mmol), benzoic acid (0.74 g, 6.0 mmol) and triphenylphosphine (2.11 g, 8.0 mmol) in toluene (20 mL) was added DIAD (1.67 mL, 8.0 mmol). After being stirred at room temperature for 4 hours, the solution was concentrated. The residue was purified by flash chromatography eluting with 0%, 5% and 20% EtOAc/hexanes provided 1.0 g of the title compound. MS calculated (M+H)+ 308, found 308.1.

Workup

  1. concentrationthe solution was concentrated
  2. customThe residue was purified by flash chromatography
  3. washeluting with 0%, 5% and 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-15bebf16ae2f430d9b1ea01f624b1c96
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Reaction notes

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