HCID 15663616, compound → HCID 10702020, compound

HRID 1587375Notes

Reaction equation

HRID 1587375 reaction equation
[N:1]12[CH2:8][C:5]([C:9](N(OC)C)=[O:10])([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[CH3:15][Li]>CCOCC>[C:9]([C:5]12[CH2:8][N:1]([CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2)(=[O:10])[CH3:15]

Participants

4

Reactant 2

HCID 15663616HCID 15663616, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 10702020HCID 10702020, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of (±) 1-azabicyclo[3.2.1]oct-5-yl-N-methyl-N-methoxycarboxamide (D3) (22.0 g; 0.11 mole) in dry ether (500 ml) was cooled to -30° C. under nitrogen and treated dropwise with methyl lithium (80.0 ml of a 1.4 M solution in diethyl ether; 0.11 mole). The rate of addition was controlled to ensure that the temperature of the reaction remained below 0° C. After stirring for 1 h at -10° C. the reaction was quenched by the addition of excess glacial acetic acid, while maintaining the temperature below -10° C. The ether solution was washed with a saturated solution of potassium carbonate. After extraction of the aqueous phase with chloroform (3×200 ml) the combined organic layers were dried over sodium sulphate and concentrated in vacuo.

Workup

  1. additionThe rate of addition
  2. customremained below 0° C
  3. customwas quenched by the addition of excess glacial acetic acid
  4. temperaturewhile maintaining the temperature below -10° C
  5. washThe ether solution was washed with a saturated solution of potassium carbonate
  6. extractionAfter extraction of the aqueous phase with chloroform (3×200 ml) the combined organic layers
  7. dry with materialwere dried over sodium sulphate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d41487007e8445a4895bbc13f2a46243
Source dataset
uspto-grants-1993_06
Patent number
US05217975

Reaction notes

Loading…