4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine → 2-(Di-tert-butoxycarbonylamino)-3-(1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-propionic acid methyl ester

HRID 2250207Notes

Reaction equation

HRID 2250207 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[N:2]1.[CH3:10][O:11][C:12](=[O:30])[C:13]([N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH2:14]>CO>[CH3:10][O:11][C:12](=[O:30])[CH:13]([N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:14][N:6]1[CH2:7][CH2:8][C:9]2[NH:1][N:2]=[CH:3][C:4]=2[CH2:5]1

Participants

4

Reactant 2

HCID 27605834,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridineHCID 10870342Methyl 2-(bis((tert-butoxy)carbonyl)amino)prop-2-enoate

Product 1

HCID 588643312-(Di-tert-butoxycarbonylamino)-3-(1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (160 mg) in 2.5 mL methanol was added 2-(di-tert-butoxycarbonylamino)-acrylic acid methyl ester (400 mg). The reaction was concentrated to approximately 1.5 mL by application of a gentle stream of nitrogen. The solution was stirred at room temperature overnight. The reaction was concentrated, dissolved in ethyl acetate, washed with brine, dried over magnesium sulfate, and concentrated. The resulting residue was pure enough to use without purification. 1H-NMR (CDCl3, 500 MHz) δ 1.44 (s, 9H), 2.73 (m, 3H), 2.91 (m, 1H), 3.06 (dd, J=13.4, 8.6, 1H), 3.22 (dd, J=13.4, 8.2, 1H), 3.54 (d, J=13.4, 1H), 3.63 (d, J=13.4, 1H), 3.71 (s, 3H), 5.11 (dd, J=8.5, 5.2, 1H), 7.25 (s, 1H). Mass spec.: 425.23 (MH)+.

Workup

  1. concentrationThe reaction was concentrated to approximately 1.5 mL by application of a gentle stream of nitrogen
  2. concentrationThe reaction was concentrated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto use without purification

Sources & evidence

ORD record
ord-5044d2cd8de3436ca4878cbbe5abb89d
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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