Triethylamine → 8-Aza-spiro[4,5]decane-8-carboxylic acid 6-{[1-(4-phenoxy-phenoxycarbonyl)-piperidine-4-oxycarbonyl]amino}-hexyl ester

HRID 618290Notes

Reaction equation

HRID 618290 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([O:23][C:24](=[O:45])[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33](OC3C=CC([N+]([O-])=O)=CC=3)=[O:34])[CH2:19][CH2:18]2)=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:47]1[C:51]2([CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)[CH2:50][CH2:49][CH2:48]1.C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:15]([N:17]2[CH2:18][CH2:19][CH:20]([O:23][C:24]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33]([N:54]3[CH2:55][CH2:56][C:51]4([CH2:50][CH2:49][CH2:48][CH2:47]4)[CH2:52][CH2:53]3)=[O:34])=[O:45])[CH2:21][CH2:22]2)=[O:16])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 224012298-Azaspiro(4.5)decane hydrochlorideHCID 542367634-[6-(4-Nitro-phenoxycarbonyloxy)-hexylcarbamoyloxy]-piperidine-1-carboxylic acid 4-phenoxyphenyl ester

Product 1

HCID 154633308-Aza-spiro[4,5]decane-8-carboxylic acid 6-{[1-(4-phenoxy-phenoxycarbonyl)-piperidine-4-oxycarbonyl]amino}-hexyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the carbonate (2.0 g, 3.2 mmol) produced in Example 5, 8-aza-spiro [4,5]-decane hydrochloride (680 mg, 3.9 mmol) and triethylamine (2.7 ml, 19 mmol) in 30 ml of anhydrous dimethylformamide was stirred under nitrogen at room temperature for 5 hours. The reaction was diluted with methylene chloride, extracted one time with 1N HCl, multiple times with saturated Na2CO3, dried (MgSO4), and the solvent removed under reduced pressure to give 1.85 g of a white solid. Recrystallization of this solid from methylene chloride-diisopropyl ether gave 1.0 g (50%) of the title compound as a white crystalline solid, mp 83-85° C.

Workup

  1. extractionextracted one time with 1N HCl, multiple times with saturated Na2CO3
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7568d245f4fd45d6a84bde117c5d736d
Source dataset
uspto-grants-1999_09
Patent number
US05952354

Reaction notes

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