Pivaloyl chloride → HCID 22458230, compound

HRID 2185566Notes

Reaction equation

HRID 2185566 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([OH:18])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CC(C)(C)C(Cl)=O.Cl.[CH3:36][NH:37][O:38][CH3:39]>C(Cl)Cl>[CH3:36][N:37]([O:38][CH3:39])[C:16](=[O:18])[CH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 62493Pivaloyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 15125403-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acid

Product 1

HCID 22458230HCID 22458230, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propionic acid (2.6 grams, 10 mmol, from Step A) and DIEA (4.4 mL, 25 mmol) in 50 mL CH2Cl2 was cooled to 0° C. Trimethylacetyl chloride (1.4 mL, 11 mmol) was added and the mixture was stirred for 1 h. Solid N,O-dimethylhydroxylamine hydrochloride (1.4 grams, 15 mmol) was added and the mixture was warmed to rt and stirred for 16 h. The solvent was removed and the product was purified by flash chromatography (125 grams silica, 2/1 hexane/EtOAc eluant) to give 1.5 grams (50%) of the title compound. 1H NMR (300 MHz, CDCl3). δ1.05-1.18 (m, 2H), 1.45 (s, 9H), 1.53-1.75 (m, 4H), 2.4-2.5 (t, 2H), 2.6-2.77 (m, 2H), 3.18 (s, 3H), 3.63 (s, 3H), 4.0-4.15 (m, 2H).

Workup

  1. stirringstirred for 16 h
  2. customThe solvent was removed
  3. customthe product was purified by flash chromatography (125 grams silica, 2/1 hexane/EtOAc eluant)

Sources & evidence

ORD record
ord-62c766c938724db0a14c145c8b5b7374
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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