Hydrochloric Acid → HCID 18316935, compound

HRID 430825Notes

Reaction equation

HRID 430825 reaction equation
Cl[O-].[F:3][C:4]([F:16])([F:15])[CH2:5][N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][C:9](=[O:14])[CH2:10]2.Cl.[C-:18]#[N:19].[K+]>O.C(OCC)C>[C:18]([C:9]1([OH:14])[CH2:8][CH:7]2[N:6]([CH2:5][C:4]([F:3])([F:15])[F:16])[CH:11]([CH2:12][CH2:13]2)[CH2:10]1)#[N:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 61739HypochloriteHCID 18519913HCID 18519913, compound

Product 1

HCID 18316935HCID 18316935, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A 50 ml 3-necked round bottom flask was equipped with a magnetic stirrer, thermometer and hypochiorite scrubber. 8-(2,2,2-Trifluoroethyl)-8-azabicyclo[3.2.1]octan-3-one (1.06 g, 5 mmol) was charged to the reaction flask followed by hydrochloric acid (5M, 10 ml) and the mixture was cooled to 0° C. Diethyl ether (7 g) was added and the mixture stirred for 5 minutes. Potassium cyanide (3.69 g, 55 mmol) was added portionwise to the stirred, cooled reaction mixture over 0.25 hour. After complete addition the resultant pink mixture was stirred for 3 hours at 5° C. Water (10 ml) was added, the organic layer separated and the aqueous phase extracted with diethyl ether (2×10 ml). The combined ether extracts were dried (Na2SO4), filtered and concentrated in vacuo (without heat) to give 3-cyano-3-hydroxy-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane (1.13 g) as a dark red oil which solidified on standing and this was used directly in Step 2.

Workup

  1. customA 50 ml 3-necked round bottom flask was equipped with a magnetic stirrer
  2. temperaturecooled
  3. customreaction mixture over 0.25 hour
  4. additionAfter complete addition the resultant pink mixture
  5. stirringwas stirred for 3 hours at 5° C
  6. customthe organic layer separated
  7. extractionthe aqueous phase extracted with diethyl ether (2×10 ml)
  8. dry with materialThe combined ether extracts were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo (without heat)

Sources & evidence

ORD record
ord-7014c30c2233451080da71ea0feaec85
Source dataset
uspto-grants-2001_11
Patent number
US06323343B1

Reaction notes

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