Ethyl 4-piperidinecarboxylate → HCID 46940322, compound

HRID 1914832Notes

Reaction equation

HRID 1914832 reaction equation
[CH3:1][C:2]1[CH:28]=[C:5]2[N:6]=[CH:7][C:8]3[CH:13]=[C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:11]([C:20]4[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=4)=[N:10][C:9]=3[N:4]2[N:3]=1.[NH:29]1[CH2:39][CH2:38][CH:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:31][CH2:30]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>O1CCOCC1.C(O)(=O)C>[CH3:1][C:2]1[CH:28]=[C:5]2[N:6]=[CH:7][C:8]3[CH:13]=[C:12]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:11]([C:20]4[CH:21]=[CH:22][C:23]([CH2:24][N:29]5[CH2:30][CH2:31][CH:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:38][CH2:39]5)=[CH:26][CH:27]=4)=[N:10][C:9]=3[N:4]2[N:3]=1

Participants

7

Reactant 4

HCID 70770Ethyl 4-piperidinecarboxylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58034334HCID 58034334, compound

Product 1

HCID 46940322HCID 46940322, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound (11-1) (1.28 g, 3.51 mmol, 1.0 eq) was dissolved in dioxane (38 mL, anhydrous). Ethyl isonipecotate (1.66 g, 10.5 mmol, 3.0 eq), glacial acetic acid (1.90 mL), and NaBH(OAc)3 (2.98 g, 14.1 mmol, 4.0 eq) were added and the reaction stirred at room temperature for 24 hours. The crude reaction was neutralized with NaHCO3 (aq.) and extracted with CHCl3 (×3). The combined organics were dried with brine and Na2SO4, and then concentrated in vacuo. The residue was purified by silica gel chromatography by eluting with a gradient of heptane and EtOAc (20% to 100% EtOAc) to afford Compound (13-1).

Workup

  1. customThe crude reaction
  2. extractionextracted with CHCl3 (×3)
  3. dry with materialThe combined organics were dried with brine and Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washby eluting with a gradient of heptane and EtOAc (20% to 100% EtOAc)

Sources & evidence

ORD record
ord-7e63140e39154e47812898f591c9f0d7
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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