Triethylamine → HCID 57619792, compound

HRID 1642495Notes

Reaction equation

HRID 1642495 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:8][C:9]#[N:10].C(N(CC)CC)C.[CH3:18][C:19]1([N:32]2[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]2)[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[C:9]([CH2:8][C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:2]1[NH:1][CH:35]1[CH2:34][CH2:33][N:32]([C:19]2([CH3:18])[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]2)[CH2:37][CH2:36]1)#[N:10]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 10990126HCID 10990126, compoundHCID 55288821HCID 55288821, compound

Product 1

HCID 57619792HCID 57619792, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution 2-[(1R,2S)-2-aminocyclohexyl]acetonitrile (HCl salt, 0.7 g, 3.32 mmol) in MeOH (10 mL) was added triethylamine (0.48 mL, 3.47 mmol) followed of tert-butyl 4-methyl-4-(4-oxo-1-piperidyl)piperidine-1-carboxylate (1 g, 3.38 mmol) at room temperature. A solution containing sodium cyanoborohydride (0.34 g, 4.93 mmol) and zinc(II) chloride (0.22 g, 1.62 mmol) in MeOH (2 mL) was then added dropwise and the mixture stirred at room temperature overnight. Concentrated in vacuo, the residue was diluted in dichloromethane (100 mL) and washed with 1N NaOH (10 mL). The aqueous phase was separated and was extracted with dichloromethane (2×20 mL). The combined organic phase was washed with brine and concentrated in vacuo to provide the title compound, which was used for the next step without any purification. MS (M+1): 419.37.

Workup

  1. additionwas then added dropwise
  2. concentrationConcentrated in vacuo
  3. additionthe residue was diluted in dichloromethane (100 mL)
  4. washwashed with 1N NaOH (10 mL)
  5. customThe aqueous phase was separated
  6. extractionwas extracted with dichloromethane (2×20 mL)
  7. washThe combined organic phase was washed with brine
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf82ed629f014029921bc2e78b56b89d
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

Loading…