Hydrochloric Acid → HCID 18316935, compound

HRID 430829Notes

Reaction equation

HRID 430829 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(OCC)C.[C-:23]#[N:24].[K+]>O>[C:23]([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:24]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 9032Potassium CyanideHCID 61739HypochloriteHCID 18519913HCID 18519913, compound

Product 1

HCID 18316935HCID 18316935, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 500 ml 3-necked round bottom flask was equipped with an overhead paddle stirrer, thermometer and hypochorite scrubber. 8-(2,2,2-Trifluoroethyl)-8-azabicyclo[3.2.1]octan-3-one (10.82 g, 50 mmol) was charged to the reaction flask followed by hydrochloric acid (5M, 100 ml) and the mixture was cooled to 0° C. Diethyl ether (70.8 g, 955 mmol) was added and the mixture stirred for 5 minutes. Potassium cyanide (36.9 g, 550 mmol) was added to the stirred reaction mixture portionwise over 0.5 hour. After complete addition the resultant pink mixture was stirred for 3 hour at about 3° C. The pH of the mixture was adjusted to 5.8 using hydrochloric acid (5M), water (50 ml) was added and the pH re-adjusted from 7 to 5.8. The organic layer was separated off and the aqueous phase was extracted with diethyl ether (2×100 ml). The ether extracts were combined, washed with highly dilute (pH 5.6) hydrochloric acid to leave a solution of 3-cyano-3-hydroxy-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]octane in diethyl ether (303 ml).

Workup

  1. customA 500 ml 3-necked round bottom flask was equipped with an overhead paddle stirrer
  2. additionAfter complete addition the resultant pink mixture
  3. stirringwas stirred for 3 hour at about 3° C
  4. additionwas added
  5. customThe organic layer was separated off
  6. extractionthe aqueous phase was extracted with diethyl ether (2×100 ml)
  7. washwashed
  8. additionwith highly dilute (pH 5.6) hydrochloric acid

Sources & evidence

ORD record
ord-74c737fa07c84542b4f6f474d26390b2
Source dataset
uspto-grants-2001_11
Patent number
US06323343B1

Reaction notes

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