8-[2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-3-(3-methylamino-propyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one → 4-{[(3-{8-[2-(6,6-Dimethyl-bicyclo(3.1.1]hept-2-yl)-ethyl]-4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-3-yl} propyl)-methyl-amino]-methyl}-4-hydroxy-piperidine-1-carboxylic Acid Tert-Butyl Ester

HRID 1294579

Reaction equation

HRID 1294579 reaction equation
[CH3:1][C:2]1([CH3:33])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:9][CH2:10][N:11]1[CH2:32][CH2:31][C:14]2([N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][N:16]([CH2:25][CH2:26][CH2:27][NH:28][CH3:29])[C:15]2=[O:30])[CH2:13][CH2:12]1.[C:34]([O:38][C:39]([N:41]1[CH2:48][CH2:47][C:44]2([O:46][CH2:45]2)[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>C(O)C>[C:34]([O:38][C:39]([N:41]1[CH2:48][CH2:47][C:44]([CH2:45][N:28]([CH2:27][CH2:26][CH2:25][N:16]2[C:15](=[O:30])[C:14]3([CH2:13][CH2:12][N:11]([CH2:10][CH2:9][CH:6]4[CH2:5][CH2:4][CH:3]5[CH2:8][CH:7]4[C:2]5([CH3:1])[CH3:33])[CH2:32][CH2:31]3)[N:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:17]2)[CH3:29])([OH:46])[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35]

Participants

4

Reactant 2

HCID 112363378-[2-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-3-(3-methylamino-propyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-oneHCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

Product 1

HCID 589064604-{[(3-{8-[2-(6,6-Dimethyl-bicyclo(3.1.1]hept-2-yl)-ethyl]-4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-3-yl} propyl)-methyl-amino]-methyl}-4-hydroxy-piperidine-1-carboxylic Acid Tert-Butyl EsterYield 89.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.6 g (5.74 mmol) of compound (24) was placed in a flask and diluted with 20 ml ethanol. To this solution was added 1.88 g (8.81 mmol) of the epoxide (32) and the mixture was heated to reflux until TLC showed complete conversion. For work-up the solvent was evaporated and the residue was taken up with ethyl acetate. After washing with aqueous potassium carbonate solution drying over sodium sulphate and concentration in vacuo the raw material was purified via flash column chromatography yielding a light yellow viscous oil (3.51 g, 5.15 mmol, 89.8% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux until TLC
  3. customFor work-up the solvent was evaporated
  4. washAfter washing with aqueous potassium carbonate solution
  5. dry with materialdrying over sodium sulphate and concentration in vacuo the raw material
  6. customwas purified via flash column chromatography

Sources & evidence

ORD record
ord-67eb260948ba40f785b3601cea271b8b
Source dataset
uspto-grants-2007_07
Patent number
US07241770B2

Linked notes

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