Acetic Acid → HCID 68408166, compound

HRID 1500323Notes

Reaction equation

HRID 1500323 reaction equation
Cl.Cl.[C:3]1([C:9]2([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:20]([O:24][C:25](=[O:31])[N:26]([CH3:30])[CH2:27][CH:28]=O)([CH3:23])([CH3:22])[CH3:21].C(B)#N.[Na].C(O)(=O)C>CO.CO.C(Cl)(Cl)Cl>[CH3:30][N:26]([CH2:27][CH2:28][N:12]1[CH2:11][CH2:10][C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:14][CH2:13]1)[C:25](=[O:31])[O:24][C:20]([CH3:21])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateHCID 67367332HCID 67367332, compoundHCID 101953985CID 101953985

Product 1

HCID 68408166HCID 68408166, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584188Chloroform methanolSolvent

Conditions

Temperature
0 °C

Procedure

7 g (1 eq) 4-phenyl-4-(pyrrolidin-1-yl)piperidine bishydrochloride were added to a solution of 4.4 g (1.1 eq) tert-butyl-methyl(2-oxoethyl)carbamate in 70 ml methanol under a nitrogen atmosphere and the reaction mixture was stirred for 10 min at 0° C. 3.62 g (2.5 eq) sodium cyanoboron hydride were then added and the mixture was stirred for 30 min at room temperature. The reaction mixture obtained was adjusted to a pH of 5-6 with acetic acid and stirred for 14 h at room temperature. The reaction course was monitored by thin-layer chromatography (10% MeOH/CHCl3). Once the conversion was complete, the methanol was distilled off, saturated NaHCO3 solution was added and the mixture obtained was extracted with chloroform (3×50 ml) and the combined organic phases were dried over Na2SO4. Following removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica gel; 50% EtOAc/heptane). 8 g (89%) of product were obtained in the form of a red oil.

Workup

  1. stirringthe mixture was stirred for 30 min at room temperature
  2. customThe reaction mixture obtained
  3. stirringstirred for 14 h at room temperature
  4. distillationthe methanol was distilled off
  5. additionsaturated NaHCO3 solution was added
  6. customthe mixture obtained
  7. extractionwas extracted with chloroform (3×50 ml)
  8. dry with materialthe combined organic phases were dried over Na2SO4
  9. customremoval of the solvent under reduced pressure
  10. customthe residue was purified by column chromatography (silica gel; 50% EtOAc/heptane)

Sources & evidence

ORD record
ord-a1913d7baf5948c68cae26eed81e746a
Source dataset
uspto-grants-2015_12
Patent number
US09206156B2

Reaction notes

Loading…