1-Benzyloxycarbonyl-2-(3-ethoxycarbonyl-2-oxopropyl)indoline → 2-(3-Ethoxycarbonyl-2-oxopropyl)indoline

HRID 1245029Notes

Reaction equation

HRID 1245029 reaction equation
[H][H].C(OC([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]1[CH2:22][C:23](=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=O)C1C=CC=CC=1.C(OC(N1C[C@H](OC)C[C@H]1CC(=O)CC(OCC)=O)=O)C1C=CC=CC=1>[OH-].[OH-].[Pd+2]>[CH2:28]([O:27][C:25]([CH2:24][C:23](=[O:30])[CH2:22][CH:14]1[CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:13]1)=[O:26])[CH3:29]

Participants

5

Reactant 3

HCID 219226511-Benzyloxycarbonyl-2-(3-ethoxycarbonyl-2-oxopropyl)indolineHCID 57501855(2S,4R)-1-Benzyloxycarbonyl-2-(3-ethoxycarbonyl-2-oxopropyl)-4-methoxypyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 219226222-(3-Ethoxycarbonyl-2-oxopropyl)indoline

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

In a similar manner to that described in Preparative Example 1(iii)′ above, a debenzylation reaction using hydrogen gas and palladium hydroxide on carbon was performed, using 1-benzyloxycarbonyl-2-(3-ethoxycarbonyl-2-oxopropyl)indoline [obtained as described in Preparative Example 5(iii)′ above] instead of (2S, 4R)-1-benzyloxycarbonyl-2-(3-ethoxycarbonyl-2-oxopropyl)-4-methoxypyrrolidine, to give the title compound as an orange oil (yield: quantitative).

Workup

  1. customa debenzylation reaction
  2. customobtained

Sources & evidence

ORD record
ord-d92abf15123f43ccb0d11987ad28a383
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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