HCID 86739194, compound → HCID 53878013, compound

HRID 2295992Notes

Reaction equation

HRID 2295992 reaction equation
[CH3:1][C:2]([CH3:44])([CH3:43])[C:3](=[O:42])[O:4][CH2:5][O:6][P:7]([CH2:19][C:20]([N:22]1[C@H:31]([C:32]([O:34]CC2C=CC=CC=2)=[O:33])[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1)=[O:21])([CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8]>CO.[Pd]>[CH3:1][C:2]([CH3:44])([CH3:43])[C:3](=[O:42])[O:4][CH2:5][O:6][P:7]([CH2:19][C:20]([N:22]1[C@H:31]([C:32]([OH:34])=[O:33])[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1)=[O:21])([CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8]

Participants

4

Reactant 1

HCID 86739194HCID 86739194, compound

Product 1

HCID 53878013HCID 53878013, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the diester product from part (b) in methanol is added to a 10% palladium on carbon catalyst and the resulting mixture is shaken in a Parr hydrogenation apparatus for several hours. The catalyst is filtered off and the methanol stripped from the filtrate. The crude product is chromatographed on silica gel to yield (S)-1,2,3,4-tetrahydro-2-[[[(2,2-dimethyl-1-oxopropoxy)methoxy](4-phenylbutyl)-phosphinyl]acetyl]-3-isoquinolinecarboxylic acid.

Workup

  1. filtrationThe catalyst is filtered off
  2. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-911ad6a407e24e36a7bb4f4f7d0008aa
Source dataset
uspto-grants-1984_01
Patent number
US04427665

Reaction notes

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