tert-Butyl 4-oxopiperidine-1-carboxylate → 1,1-Dimethylethyl 4-[[2-(2-amino-3-pyridinyl)ethyl]amino]-1-piperidinecarboxylate

HRID 1453958Notes

Reaction equation

HRID 1453958 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:5]([NH2:10])=[N:6][CH:7]=[CH:8][CH:9]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(O)(=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([NH:1][CH2:2][CH2:3][C:4]2[C:5]([NH2:10])=[N:6][CH:7]=[CH:8][CH:9]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 54105929844503-06-6

Product 1

HCID 685357711,1-Dimethylethyl 4-[[2-(2-amino-3-pyridinyl)ethyl]amino]-1-piperidinecarboxylateYield 42.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 3-(2-aminoethyl)-2-aminopyridine (0.122 g, 0.88 mmol) and 1-t-butoxycarbonyl 4-piperidone (0.177 g, 0.88 mmol) in dichloroethane (3 mL) containing 2 drops of acetic acid was treated with sodium triacetoxyborohydride (0.28 g, 1.33 mmol) at 20-75° C. until starting material was no longer consumed. The reaction was worked up with saturated sodium bicarbonate and methylene chloride, and dried over sodium sulfate. The crude product was purified by chromatography (silica gel, 0-10% {0.1% ammonium hydroxide in methanol) in methylene chloride, gradient elution) to produce the title compound (0.119 g) as a yellow oil. MS 321 (M+1).

Workup

  1. customwas no longer consumed
  2. dry with materialdried over sodium sulfate
  3. customThe crude product was purified by chromatography (silica gel, 0-10% {0.1% ammonium hydroxide in methanol) in methylene chloride
  4. washgradient elution)

Sources & evidence

ORD record
ord-e64ae6b86b49456fb572f5d2fcbe7ae8
Source dataset
uspto-grants-2009_01
Patent number
US07476665B2

Reaction notes

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