Hydrochloric Acid → HCID 68982736, compound

HRID 748629Notes

Reaction equation

HRID 748629 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([F:23])[CH:15]=2)[CH2:10][CH:9]1[C:24](C)(C)[O:25][SiH2]C(C)(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C([O-])(O)=O.[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([F:23])[CH:15]=2)[CH2:10][CH:9]1[CH2:24][OH:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131726965HCID 131726965, compound

Product 1

HCID 68982736HCID 68982736, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 30 g of 2-(tert-butyl-dimethyl-silanyloxymethyl)-4-(3-fluoro-5-nitro-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (5) in 240 mL MeOH at 0° C. was added 2.6 mL of 1N HCl, dropwise. The reaction mixture was warmed up to room temperature and stirred for an additional 4 hours. After cooling to 0° C., to the reaction mixture was added 5 g of NaHCO3 and the mixture was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated to afford 22.7 g of 4-(3-fluoro-5-nitro-phenoxy)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tertbutyl ester (6).

Workup

  1. temperatureAfter cooling to 0° C., to the reaction mixture
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7f5b498ca1ce424ea02711f3942eda2f
Source dataset
uspto-grants-2008_07
Patent number
US07399866B2

Reaction notes

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