Triethylamine → 2,3-dihydro-3-[[(methylamino)carbonyl]amino]spiro[1H-indene-1,4'-piperidine]-1'-carboxylic acid 1,1-dimethylethyl ester

HRID 1902165Notes

Reaction equation

HRID 1902165 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]([NH2:22])[CH2:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].C(N(CC)CC)C.[CH3:30][N:31]=[C:32]=[O:33].C(Cl)Cl.C(OCC)(=O)C>C(Cl)Cl>[CH3:4][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]([NH:22][C:32]([NH:31][CH3:30])=[O:33])[CH2:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 18476131Tert-butyl 3-amino-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylateHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 538278502,3-dihydro-3-[[(methylamino)carbonyl]amino]spiro[1H-indene-1,4'-piperidine]-1'-carboxylic acid 1,1-dimethylethyl esterYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of the intermediate obtained in Step A (263 mg, 0.865 mmol) and triethylamine (0.145 ml, 1.03 mmol) in methylene chloride was added methylisocyanate (0.061 ml, 1.03 mmol). The reaction mixture was stirred overnight and then applied to a flash chromatography column. Flash chromatography (silica gel, methylene chloride/ethyl acetate 1:1) provided the title compound (206 mg, 0.57 mmol).

Sources & evidence

ORD record
ord-febc325daf0c42969e40fec289a2b4d6
Source dataset
uspto-grants-1996_11
Patent number
US05578593

Reaction notes

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