Piperidine → (2S)-2-Amino-3-(4-(tert-butoxy)phenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamide

HRID 707505Notes

Reaction equation

HRID 707505 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:33]C(=O)OCC2C3C=CC=CC=3C3C2=CC=CC=3)[C:14](=[O:32])[N:15]([CH2:24][CH:25]([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[N:18]=2)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].N1CCCCC1>ClCCl>[NH2:33][C@@H:13]([CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:11][CH:10]=1)[C:14]([N:15]([CH2:24][CH:25]([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[N:18]=1)=[O:32]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 1181624949H-Fluoren-9-ylmethyl N-((1S)-2-(4-(tert-butoxy)phenyl)-1-((2,2-diethoxyethyl)((6-fluoropyridin-2-yl)methyl)carbamoyl)ethyl)carbamate

Product 1

HCID 118162420(2S)-2-Amino-3-(4-(tert-butoxy)phenyl)-N-(2,2-diethoxyethyl)-N-((6-fluoropyridin-2-yl)methyl)propanamideYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixed solution of 9H-fluoren-9-ylmethyl N-((1S)-2-(4-(tert-butoxy)phenyl)-1-((2,2-diethoxyethyl)((6-fluoropyridin-2-yl)methyl)carbamoyl)ethyl)carbamate (1.37 g, 2.00 mmol) described in Production Example 2-1 and dichloromethane (7.0 mL) was added piperidine (7.0 mL) at room temperature. The resultant mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under a reduced pressure, and the resultant residue was purified by NH silica gel column chromatography (ethyl acetate) to give the title compound (881 mg, yield: 95%).

Workup

  1. concentrationThe reaction mixture was concentrated under a reduced pressure
  2. customthe resultant residue was purified by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-d03f3a9d50a34f5c88db94394d7b8ffd
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

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