4-Amino-1-Boc-piperidine → HCID 21064718, compound

HRID 1243798Notes

Reaction equation

HRID 1243798 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1>CN(C=O)C>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:13]([NH:12][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 12682914-Amino-1-Boc-piperidineHCID 21928118HCID 21928118, compound

Product 1

HCID 21064718HCID 21064718, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a sealed tube was added 4-oxiranylmethoxy-pyridine (80 mg, 0.529 mmol) in 4 mL of DMF, followed by the addition of 4-amino-1-N-boc-piperidine (148 mg, 0.739 mmol). The reaction mixture was stirred at 80° C. for 48 h. The reaction mixture was concentrated in vacuo. The residue was loaded to a flash chromatography column. The column was eluted with 0–5% 2M NH3 in MeOH/CH2Cl2. The product fractions were collected and concentrated to afford 68 mg (36.6%) of 4-[2-hydroxy-3-(pyridin-4-yloxy)-propylamino]-piperidine-1-carboxylic acid tert-butyl ester as a light brown oil. (TLC: Rf=0.15, 5% 2M NH3 in MeOH/CH2Cl2, UV). ES+ 352.43 m/z (MH+)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washThe column was eluted with 0–5% 2M NH3 in MeOH/CH2Cl2
  3. customThe product fractions were collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c1b06d15f4904a6da157b3918827507b
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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