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tert-Butyl 4-oxopiperidine-1-carboxylate → 3-[2-(1-t-Butoxycarbonyl-4-piperidinylamino)ethyl]-2-aminopyridine

HRID 1453958
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 541059293-(2-Aminoethyl)pyridin-2-amine

Product 1

HCID 685357713-[2-(1-t-Butoxycarbonyl-4-piperidinylamino)ethyl]-2-aminopyridineYield 42.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalyst
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07476665B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes