Ammonia → Benzyl 4-[(3-amino-3-oxopropyl)(tert-butoxycarbonyl)amino]piperidin-1-carboxylate

HRID 2366554Notes

Reaction equation

HRID 2366554 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][CH2:19][C:20]([OH:22])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:32]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.N>CN(C=O)C>[NH2:32][C:20](=[O:22])[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH:14]1[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 68418183HCID 68418183, compound

Product 1

HCID 68425948Benzyl 4-[(3-amino-3-oxopropyl)(tert-butoxycarbonyl)amino]piperidin-1-carboxylateYield 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-{1-[(benzyloxy)carbonyl]piperidin-4-yl}-N-(tert-butoxycarbonyl) -β-alanine (4.06 g) obtained in Example 45b), WSC (1.92 g) and HOBt.NH3 (1.52 g) in DMF (40 mL) was stirred overnight at room temperature, and DMF was distilled off under reduced pressure. The residue was diluted with dichloromethane, washed with an aqueous saturated sodium bicarbonate solution and saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (from ethyl acetate/hexane=1/1 to ethyl acetate) to obtain the title compound (3.38 g, 83%) as a white amorphous powder.

Workup

  1. distillationDMF was distilled off under reduced pressure
  2. additionThe residue was diluted with dichloromethane
  3. washwashed with an aqueous saturated sodium bicarbonate solution and saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (from ethyl acetate/hexane=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-464ff1a859504909b9f46953ad6d9deb
Source dataset
uspto-grants-2014_04
Patent number
US08697865B2

Reaction notes

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