tert-butyl N-methyl-N-(3-oxopropyl)carbamate → HCID 68490529, compound

HRID 1500341Notes

Reaction equation

HRID 1500341 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][CH:12]=O)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Cl.Cl.[CH3:16][N:17]([CH3:29])[C:18]1([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(B)#N.[Na].CO.C(Cl)(Cl)Cl>CO.C(O)(=O)C>[CH3:16][N:17]([CH3:29])[C:18]1([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][N:21]([CH2:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 10442454tert-butyl N-methyl-N-(3-oxopropyl)carbamateHCID 21584188Chloroform methanolHCID 67369868HCID 67369868, compoundHCID 101953985CID 101953985

Product 1

HCID 68490529HCID 68490529, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

6.4 g (1.3 eq) tert-butyl methyl(3-oxopropyl)carbamate were added to a solution of 7.5 g (1 eq) N,N-dimethyl-4-(thiophen-2-yl)piperidin-4-amine bis hydrochloride in 75 ml methanol at 0° C. and the reaction mixture was stirred for 15 min at 0° C. 4.9 g (3 eq) sodium cyanoboron hydride were then added in portions and the mixture was stirred for 90 min at room temperature. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). As the conversion was not yet complete, the pH of the reaction mixture was adjusted to 5-6 with acetic acid and the mixture was stirred for 12 h at room temperature. Once the conversion was complete, the methanol was distilled off, water was added, the mixture obtained was extracted with IPA/chloroform (2×100 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; 5% MeOH/CHCl3). 8.5 g (84%) of product were obtained.

Workup

  1. stirringthe mixture was stirred for 90 min at room temperature
  2. stirringthe mixture was stirred for 12 h at room temperature
  3. distillationthe methanol was distilled off
  4. additionwater was added
  5. customthe mixture obtained
  6. extractionwas extracted with IPA/chloroform (2×100 ml)
  7. dry with materialthe combined organic phases were dried over Na2SO4
  8. customremoval of the solvent under reduced pressure
  9. customthe residue was purified by column chromatography (silica gel; 5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-7980c59463764d378caaf4f9efea57e1
Source dataset
uspto-grants-2015_12
Patent number
US09206156B2

Reaction notes

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