Triethylamine → HCID 66798689, compound

HRID 1193311Notes

Reaction equation

HRID 1193311 reaction equation
[CH3:1][C:2]1([CH3:13])[CH:11]([NH2:12])[CH2:10][CH2:9][C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3]1.C(N(CC)CC)C.[CH:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:28][C:29](Cl)=[O:30])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.ClCCl>[CH3:1][C:2]1([CH3:13])[CH:11]([NH:12][C:29](=[O:30])[O:28][CH2:27][C:24]2[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:9][C:4]2([O:5][CH2:6][CH2:7][O:8]2)[CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 66799292HCID 66799292, compound

Product 1

HCID 66798689HCID 66798689, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

7,7-Dimethyl-1,4-dioxaspiro[4.5]decan-8-amine (1.3 g, 7.027 mmol, 1 eq) was dissolved in triethylamine (3.89 ml, 28.10 mmol, 4 eq) and dichloromethane (25 ml) and added dropwise at 0° C. to a 50% solution of Cbz-Cl (2.56 ml, 8.432 mmol, 1.2 eq) in toluene, and the mixture was then stirred for 2 h at RT. After monitoring by thin-layer chromatography, the reaction mixture was diluted with dichloromethane (100 ml), washed with water (75 ml), sat. NH4Cl solution (75 ml) and sat. NaCl solution (75 ml), dried over sodium sulfate and concentrated under reduced pressure. After purification by column chromatography (silica gel, 15% ethyl acetate in hexane), the desired product was obtained in the form of a colourless, viscous oil. Yield: 34% (960 mg, 3.0 mmol).

Workup

  1. washwashed with water (75 ml), sat. NH4Cl solution (75 ml) and sat. NaCl solution (75 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customAfter purification by column chromatography (silica gel, 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e73d693a731040449562480c257587e3
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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