Piperidine → (13S,16R)-16-Amino-13-isopropyl-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),18(22),19-trien-15-one

HRID 2040002Notes

Reaction equation

HRID 2040002 reaction equation
[CH:1]([C@@H:4]1[NH:23][C:22](=[O:24])[C@H:21]([NH:25]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)[CH2:20][C:19]2=[CH:43][CH:44]=[C:16]([CH:17]=[CH:18]2)[O:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5]1)([CH3:3])[CH3:2].N1CCCCC1>CO.[Pd]>[NH2:25][C@@H:21]1[CH2:20][C:19]2=[CH:18][CH:17]=[C:16]([CH:44]=[CH:43]2)[O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C@H:4]([CH:1]([CH3:2])[CH3:3])[NH:23][C:22]1=[O:24]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 866559669H-Fluoren-9-yl-methyl ((13S,16R)-13-isopropyl-15-oxo-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),4,18(22),19-tetraen-16-yl)carbamate

Product 1

HCID 67028556(13S,16R)-16-Amino-13-isopropyl-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),18(22),19-trien-15-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.87 (1.46 mmol) of 9H-fluoren-9-yl-methyl ((13S,16R)-13-isopropyl-15-oxo-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),4,18(22),19-tetraen-16-yl)-carbamate and 0.16 g of 10% Pd/C in 100 ml of methanol was stirred under a hydrogen atmosphere at RT. After stirring overnight and addition of 0.5 ml of piperidine, stirring was continued for 2 h, and the mixture was filtered and freed of solvent. The residue was separated by preparative HPLC. The required fractions were combined and freeze dried. 0.18 g of the title compound was obtained as trifluoroacetate.

Workup

  1. stirringAfter stirring overnight
  2. stirringstirring
  3. filtrationthe mixture was filtered
  4. customThe residue was separated by preparative HPLC
  5. customfreeze dried

Sources & evidence

ORD record
ord-7e0f46dbe4aa48639fae20aeb0c53f53
Source dataset
uspto-grants-2013_11
Patent number
US08580777B2

Reaction notes

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