HCID 69831996, compound → 1'-(tert-Butoxycarbonyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-carboxylic acid

HRID 2229266Notes

Reaction equation

HRID 2229266 reaction equation
C([O:3][C:4]([CH:6]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:8]2([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH2:7]1)=[O:5])C>CO.C(OCC)(=O)C.[Pd]>[CH3:19][C:17]([CH3:20])([O:16][C:14]([N:11]1[CH2:10][CH2:9][C:8]2([C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:6]([C:4]([OH:5])=[O:3])[CH2:7]2)[CH2:13][CH2:12]1)=[O:15])[CH3:18]

Participants

5

Reactant 1

HCID 69831996HCID 69831996, compound

Product 1

HCID 184670621'-(tert-Butoxycarbonyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-carboxylic acidYield 916.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of Pd/C (300 mg) in methanol (20 ml) and ethyl acetate (10 ml) was added the title compound (1.2 g, 3.6 mmol) from Step B. The reaction mixture was purged with hydrogen and then stirred under a hydrogen balloon for 1 h. The mixture was filtered through celite and concentrated to give the title compound (1.1 g, 33 mmol). 1HNMR (200 MHz, CDCl3): 7.50-7.42 (m, 1 H), 7.34-7.12 (m, 3 H), 4.22-4.04 (m, 3 H), 3.06-2.84 (m, 2 H), 2.40 (d, 2 H), 1.88-1.6 (m, 4 H), 1.50 (s, 9 H).

Workup

  1. customThe reaction mixture was purged with hydrogen
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c2d5a1f5674843249e9b751bc0d86ce3
Source dataset
uspto-grants-2002_07
Patent number
US06420376B1

Reaction notes

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