Hydrochloric Acid → HCID 68310801, compound

HRID 2405747Notes

Reaction equation

HRID 2405747 reaction equation
C(OC(=O)[NH:7][C:8]12[CH2:15][CH:14]3[CH2:16][C:10]([C:17](=[O:19])[NH2:18])([CH2:11][CH:12]1[CH2:13]3)[CH2:9]2)(C)(C)C.Cl>ClCCl>[NH2:7][C:8]12[CH2:15][CH:14]3[CH2:16][C:10]([C:17]([NH2:18])=[O:19])([CH2:11][CH:12]1[CH2:13]3)[CH2:9]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86706046HCID 86706046, compound

Product 1

HCID 68310801HCID 68310801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Carbamoylhexahydro-2,5-methanopentalen-3a-yl)carbamic acid tert-butyl ester (1.8 g) dissolved in dichloromethane (50 ml), 11 equivalents of HCl (4M in dioxane) added and the mixture stirred at room temperature overnight. LCMS: amine is fully deprotected. The reaction solution was concentrated by rotary evaporation, the HCl salt of the amine was released with 50 ml of saturated Na2CO3 solution+3 ml of 2M NaOH, and the mixture was extracted a total of 8 times with 20 ml of dichloromethane and once with EtOAc. The organic solutions were combined, dried over MgSO4, filtered, concentrated by rotary evaporation and dried under high vacuum. The residue (0.91 g) was used further without further workup.

Workup

  1. concentrationThe reaction solution was concentrated by rotary evaporation
  2. extractionthe mixture was extracted a total of 8 times with 20 ml of dichloromethane
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-addcf69d2fe547c781d3fb63edc2429f
Source dataset
uspto-grants-2014_08
Patent number
US08809325B2

Reaction notes

Loading…