HCID 131735752, compound → HCID 131735751, compound

HRID 2202302Notes

Reaction equation

HRID 2202302 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:13][C:14]([C@H:16]2[C:25]3[C:20](=[CH:21][C:22]([O:26][CH3:27])=[CH:23][CH:24]=3)[CH2:19][CH2:18][N:17]2[C:28]([C@@H:30]2[CH2:32][C@H:31]2[CH2:33][C:34]([O:36]CC2C=CC=CC=2)=[O:35])=[O:29])=[O:15])[CH:5]=[C:6]([F:12])[C:7]=1[Si:8]([CH3:11])([CH3:10])[CH3:9]>CO.[C].[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH:13][C:14]([C@H:16]2[C:25]3[C:20](=[CH:21][C:22]([O:26][CH3:27])=[CH:23][CH:24]=3)[CH2:19][CH2:18][N:17]2[C:28]([C@@H:30]2[CH2:32][C@H:31]2[CH2:33][C:34]([OH:36])=[O:35])=[O:29])=[O:15])[CH:5]=[C:6]([F:12])[C:7]=1[Si:8]([CH3:9])([CH3:10])[CH3:11]

Participants

4

Reactant 1

HCID 131735752HCID 131735752, compound

Product 1

HCID 131735751HCID 131735751, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 2-((1S,2R)-2-((R)-1-((3,5-difluoro-4-(trimethylsilyl)phenyl)carbamoyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)cyclopropyl)acetate (63 mg, 0.10 mmol) and 10% palladium-carbon (11.1 mg, 0.10 mmol, 50%, wet) in MeOH (20 mL) was stirred at room temperature for 2 hr under hydrogen atmosphere (1 atm). The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane) to give the title compound (40.0 mg, 0.077 mmol, 74.6%) as a white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-32fd2a2d84344a0180830ac68d468102
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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