Ethyl 4-piperidinecarboxylate → HCID 22729501, compound

HRID 1747274Notes

Reaction equation

HRID 1747274 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=O.[NH:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][N:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 27630013-AminoisonicotinaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22729501HCID 22729501, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

3-Amino-pyridine-4-carbaldehyde (5.00 g, 40.9 mmol) was dissolved in DCM (60 mL), ethyl 4-piperidinecarboxylate (7.57 mL, 49.1 mmol) and NaBH(OAc)3 (10.4 g, 49.1 mmol) were added and the reaction mixture was heated in a microwave reactor at 60° C. for 5 min. The reaction mixture was diluted with DCM (100 mL) and quenched with sat aq Na2CO3 (50 mL). The organic fraction was washed with sat aq NH4Cl (30 mL). The combined aq fractions were extracted with DCM (2×50 mL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the crude title compound as a yellow gum (11.3 g). LCMS (ES+): 264.1 [MH]+.

Workup

  1. customquenched with sat aq Na2CO3 (50 mL)
  2. washThe organic fraction was washed with sat aq NH4Cl (30 mL)
  3. extractionThe combined aq fractions were extracted with DCM (2×50 mL)
  4. dry with materialthe combined organic fractions were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02d63982ef114886ae86c45434cf17da
Source dataset
uspto-grants-2015_10
Patent number
US09150574B2

Reaction notes

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