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 2274540Notes

Reaction equation

HRID 2274540 reaction equation
C1C2C(OC(=O)[N:16](C)[C@@H:17]3[CH2:36][C:35]4=[CH:37][CH:38]=[C:32]([CH:33]=[CH:34]4)[O:31][CH2:30][CH:29]=[CH:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:22][CH2:21][C@H:20]([CH:39]([CH3:41])[CH3:40])[NH:19][C:18]3=[O:42])C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CO.[Pd]>[NH2:16][C@@H:17]1[CH2:36][C:35]2=[CH:34][CH:33]=[C:32]([CH:38]=[CH:37]2)[O:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:22][CH2:21][C@H:20]([CH:39]([CH3:40])[CH3:41])[NH:19][C:18]1=[O:42]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 867279389H-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-924ce1003fe94bac8b46a6850a7edae4
Source dataset
uspto-grants-2015_09
Patent number
US09126955B2

Reaction notes

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