(S)-[1-(2-Benzyloxy-5-cyano-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester → (S)-[1-(5-cyano-2-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester

HRID 567031Notes

Reaction equation

HRID 567031 reaction equation
C([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([C:36]#[N:37])[C:22]([N:23]3[CH2:27][CH2:26][C@H:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:24]3)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:38])C1C=CC=CC=1>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:36]([C:21]1[C:22]([N:23]2[CH2:27][CH2:26][C@H:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:24]2)=[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]2=[C:17]([CH:20]=1)[C:18](=[O:19])[N:9]([OH:8])[C:10]3=[O:38])#[N:37]

Participants

4

Reactant 1

HCID 86756246(S)-[1-(2-Benzyloxy-5-cyano-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester

Product 1

HCID 86756249(S)-[1-(5-cyano-2-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl esterYield 42.8%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalyst2×HCID 887MethanolSolvent

Procedure

Following the procedure of Example 55, (S)-[1-(2-benzyloxy-5-cyano-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester (0.17 g, 0.31 mmol, from Example E2) and a 5% Pd/BaSO4 (0.50 g) were reacted, with an additional 0.045 g and 0.030 g of 5% Pd/BaSO4 in methanol (50 mL) being added after 100 hours and 120 hours, respectively, to give 0.056 g of (S)-[1-(5-cyano-2-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester. This material was used in the next step without further purification.

Workup

  1. additionbeing added after 100 hours and 120 hours

Sources & evidence

ORD record
ord-5f4714eed5704d0e9a87a187441b36c1
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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