Hydrochloric Acid → HCID 68850190, compound

HRID 1984890Notes

Reaction equation

HRID 1984890 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)(C)(C)C.C(N(C(C)C)CC)(C)C.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([Cl:33])(=[O:32])=[O:31])=[C:26]([O:34][C:35]([F:38])([F:37])[F:36])[CH:25]=1.C([O-])(O)=O.[Na+].Cl>C(Cl)Cl.C(Cl)(Cl)Cl.CCOC(C)=O>[ClH:33].[Br:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:10]2[CH2:11][CH2:12][CH:8]([NH2:7])[CH2:9]2)(=[O:32])=[O:31])=[C:26]([O:34][C:35]([F:37])([F:36])[F:38])[CH:25]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27364214-Bromo-2-(Trifluoromethoxy)Benzene-1-Sulfonyl ChlorideHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Product 1

HCID 68850190HCID 68850190, compoundYield 80.1%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of pyrrolidin-3-yl-carbamic acid tert-butyl ester (1.00 g, 5.37 mmol) in CH2Cl2 (10 mL) was added diisopropylethylamine (1.96 mL, 5.92 mmol). The mixture was cooled at 0° C. and a solution of 4-bromo-2-trifluoromethoxy-benzenesulfonyl chloride (2.01 g, 5.92 mmol) in CH2Cl2 (10 mL) was added below 10° C. The reaction mixture was stirred at 4° C. for 15 min, dissolved in CHCl3 and saturated aqueous NaHCO3. The two phases were separated, the aqueous layer was extracted with CHCl3 (twice). The combined organic layer was dried over MgSO4, filtered, concentrated, and dried under reduced pressure to give a pale brown solid. To a solution of the above solid in CHCl3 (50 mL) was added 4 M hydrogen chloride in EtOAc (50 mL). The mixture was stirred at ambient temperature for 1 hr, filtered, washed with EtOAc, and dried under reduced pressure to give 1-(4-bromo-2-trifluoromethoxy-benzenesulfonyl)-pyrrolidin-3-ylamine hydrochloride (1.83 g, 80%) as a white solid.

Workup

  1. customThe two phases were separated
  2. extractionthe aqueous layer was extracted with CHCl3 (twice)
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried under reduced pressure
  7. customto give a pale brown solid
  8. stirringThe mixture was stirred at ambient temperature for 1 hr
  9. filtrationfiltered
  10. washwashed with EtOAc
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-057fef3b962d44c29e2d86c4c7ef923d
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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