HCID 66953749, compound → HCID 46231489, compound

HRID 1424596Notes

Reaction equation

HRID 1424596 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][C:16]3([CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]3O)[CH2:15]1)=[O:13])[CH2:8]2>C(O)C.[OH-].[OH-].[Pd+2]>[CH:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][C:16]3([CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20]3)[CH2:15]1)=[O:13])[CH2:10]2

Participants

4

Reactant 1

HCID 66953749HCID 66953749, compound

Product 1

HCID 46231489HCID 46231489, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(2-adamantyl)-1-hydroxy-1,3-dihydrospiro[indene-2,3′-piperidine]-1′-carboxamide (20 mg, 0.052 mmol) in ethanol (3 mL) was added Pd(OH)2 (10 mg), then the reaction mixture was stirred for 4 h at rt under a hydrogen atmosphere. The reaction mixture was filtered and the filtrate was evaporated to give a residue, which was purified by preparative HPLC to afford N-(2-adamantyl)-1,3-dihydrospiro[indene-2,3′-piperidine]-1′-carboxamide (5 mg, 29%): LC-MS Method 5 tR=3.057 min, m/z=365.2; 1H NMR (CD3OD, 400 MHz): δ=1.55 (m, 2H), 1.66 (m, 2H), 1.78 (m, 7H), 1.84 (m, 7H), 2.69-2.83 (m, 4H), 3.21 (s, 2H), 3.45 (m, 2H), 3.77 (s, 1H), 7.09 (m, 2H), 7.14 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customto give a residue, which
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-31d2108a5f2945c4b1389e9b46924a73
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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