HCID 69382578, compound → HCID 21099228, compound

HRID 1351749Notes

Reaction equation

HRID 1351749 reaction equation
C([O:8][C:9]([C:11]1[C:19]([CH3:20])=[C:18]2[C:14]([C:15]3[CH2:24][CH2:23][O:22][C:21]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])([CH2:25][CH2:26][CH3:27])[C:16]=3[NH:17]2)=[C:13]([C:34]#[N:35])[CH:12]=1)=[O:10])C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO.CCOC(C)=O>[C:34]([C:13]1[CH:12]=[C:11]([C:9]([OH:10])=[O:8])[C:19]([CH3:20])=[C:18]2[C:14]=1[C:15]1[CH2:24][CH2:23][O:22][C:21]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])([CH2:25][CH2:26][CH3:27])[C:16]=1[NH:17]2)#[N:35]

Participants

4

Reactant 1

HCID 69382578HCID 69382578, compound

Product 1

HCID 21099228HCID 21099228, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A 500 mL Parr flask was charged with 5-cyano-1-ethoxycarbonylmethyl-8-methyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indole-7-carboxylic acid benzyl ester (14.24 g, 0.030 mol), 1:1 MeOH/EtOAc (180 mL), and Pd(OH)2 (20% on C, 3.02 g). The flask was shaken on a Parr shaker at 5 psi above ambient pressure for 30 minutes. The reaction mixture was filtered through a pad of Celite, washed with methanol and concentrated. Trituration with hexanes yielded 11.11 g (96.4%) of an off-white powder. 1H NMR (CDCl3) δ 10.21 (br s, 1H), 8.22 (s, 1H), 4.22 (m, 2H), 4.00 (m, 2H), 3.09 (m, 4H), 2.89 (s, 3H), 2.00 (m, 2H), 1.30 (m, 5H), 0.90 (t, J=7.6 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washwashed with methanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c58074c1a8cb4770b3a3f0e9b7ce9615
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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