Cyclopropanecarboxaldehyde → HCID 57848224, compound

HRID 736913Notes

Reaction equation

HRID 736913 reaction equation
[BH3-]C#N.[Na+].[N:5]1([CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[CH:24]1([CH:27]=O)[CH2:26][CH2:25]1>CCO>[CH:24]1([CH2:27][N:8]2[CH2:7][CH2:6][N:5]([CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[CH2:10][CH2:9]2)[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 17750358tert-Butyl 4-(piperazin-1-yl)piperidine-1-carboxylate

Product 1

HCID 57848224HCID 57848224, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.26 g (20.0 mmol) NaBH3CN were added in 4 batches at RT to a solution of 1.71 g (5.0 mmol) tert. butyl 4-piperazin-1-yl-piperidine-1-carboxylate and 0.75 mL (10.0 mmol) cyclopropanecarbaldehyde in 100 mL of EtOH and the reaction mixture was stirred overnight at RT. The mixture was evaporated down i.vac., the residue was taken up in saturated NaHCO3 solution, extracted exhaustively with EtOAc and the organic phase was dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:0.5).

Workup

  1. customThe mixture was evaporated down i.vac
  2. extractionextracted exhaustively with EtOAc
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customwas purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:0.5)

Sources & evidence

ORD record
ord-41770f3a181d4254b270f755f1060eac
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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