Acetyl chloride → HCID 53485869, compound

HRID 1880343Notes

Reaction equation

HRID 1880343 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]2[O:10][C:11]3([CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[CH2:12][C:13](=[O:14])[C:7]2=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.C(Cl)(=O)C>CO>[C:1]([N:5]1[CH:9]=[C:8]2[O:10][C:11]3([CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[CH2:12][C:13](=[O:14])[C:7]2=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 66843844tert-Butyl 2'-tert-butyl-7'-oxo-6',7'-dihydro-1H,2'H-spiro[piperidine-4,5'-pyrano[3,2-c]pyrazole]-1-carboxylate

Product 1

HCID 53485869HCID 53485869, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a 200 L reactor was charged: tert-butyl 2′-tert-butyl-7′-oxo-6′,7′-dihydro-2′H-spiro[piperidine-4,5′-pyrano[3,2-c]pyrazole]-1-carboxylate (8.3 kg, 22.8 moles), ethyl acetate (89 L), and methanol (24 L). Solution was cooled to 0° C., and acetyl chloride (11.0 L, 155 moles) was added over 30 minutes. After addition, reaction was allowed to warm to ambient temperature and react for 4 hours. Heated solution in order to distill to a 41 L reaction volume, slowly refilling with ethyl acetate (˜0.22 L) until an internal temperature of 72° C. was reached. Cooled to ambient temperature over 3 hours, filtered the solids through a Nutsche Filter, washed with ethyl acetate (5.3 L), and dried under vacuum at 50° C. for 12 hours. Isolated 6.6 kg (22.0 moles, 96%) of 2′-tert-butyl-2′H-spiro[piperidine-4,5′-pyrano[3,2-c]pyrazol]-7′(6′H)-one as a white crystalline solid.

Workup

  1. additionTo a 200 L reactor was charged
  2. additionAfter addition, reaction
  3. temperatureto warm to ambient temperature
  4. customreact for 4 hours
  5. distillationHeated solution in order to distill to a 41 L reaction volume
  6. customslowly refilling with ethyl acetate (˜0.22 L) until an internal temperature of 72° C.
  7. temperatureCooled to ambient temperature over 3 hours
  8. filtrationfiltered the solids through a Nutsche
  9. filtrationFilter
  10. washwashed with ethyl acetate (5.3 L)
  11. customdried under vacuum at 50° C. for 12 hours

Sources & evidence

ORD record
ord-0f2a0a2bba5b4d0cbe684b986e39c415
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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