Hydrochloric Acid → HCID 59730568, compound

HRID 130622Notes

Reaction equation

HRID 130622 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]([OH:15])=[O:14])[C@@H:9]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7])([CH3:4])(C)C.Cl.C([O-])(O)=O.[Na+:27].ClC(OC[C:33]1[CH:38]=[CH:37]C=[CH:35][CH:34]=1)=O>O1CCOCC1>[Na+:27].[CH2:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]([O-:15])=[O:14])[C@@H:9]1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:7])[C:4]1[CH:37]=[CH:38][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 57354967(2R,3R)-1-(tert-Butoxycarbonyl)-2-phenylpyrrolidine-3-carboxylic acid

Product 1

HCID 59730568HCID 59730568, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

trans-2-Phenyl-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester obtained from preparatory example 8 (10.1 g, 34.8 mmol) was stirred in 1,4-dioxane (145 mL) at 0° C. 6 M HCl (29 mL, 174 mmol) was added and the mixture was slowly warmed to rt and stirred for 16 h. The mixture was then cooled to 0° C. and solid NaHCO3 was carefully added until the aqueous layer was saturated. Benzyl chloroformate was added and the mixture was stirred vigorously at 0° C. for 1 hr, and at rt for 20 h. The suspension was then filtered and the solids were dried under vacuum to give 6.54 g (55%) of the title compound. MS APCI: [M+H]+=326.1

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. stirringthe mixture was stirred vigorously at 0° C. for 1 hr
  3. waitat rt for 20 h
  4. filtrationThe suspension was then filtered
  5. customthe solids were dried under vacuum

Sources & evidence

ORD record
ord-ffb09151c70f4de7a7f6369859a271b1
Source dataset
uspto-grants-2008_06
Patent number
US07381741B2

Reaction notes

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