Diethylamine → (5R)-5-((benzyloxy)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,5,6-tetrahydropyridine-2-carboxamide

HRID 627186Notes

Reaction equation

HRID 627186 reaction equation
C(NCC)C.[CH2:6]([O:13][NH:14][C@H:15]1[CH2:20][N:19](C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[CH:18]([C:38](=[O:40])[NH2:39])[C:17]([CH2:41][O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])=[CH:16]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[CH2:6]([O:13][NH:14][C@H:15]1[CH2:20][NH:19][CH:18]([C:38]([NH2:39])=[O:40])[C:17]([CH2:41][O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:44])[CH3:45])=[CH:16]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 89851827(5R)-(9H-fluoren-9-yl)methyl 5-((benzyloxy)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-carbamoyl-5,6-dihydropyridine-1 (2H)-carboxylate2×

Product 1

HCID 123580399(5R)-5-((benzyloxy)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,5,6-tetrahydropyridine-2-carboxamideYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylamine (0.824 mL, 7.89 mmol) was added to a solution of (5R)-(9H-fluoren-9-yl)methyl 5-((benzyloxy)amino)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-carbamoyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 162, 0.968 g, 1.58 mmol) in DCM (20 mL) and the resulting solution was allowed to stir at room temperature overnight. The volatiles were removed by evaporation and the residue was purified on silica gel (0-12%, MeOH/DCM, UV 220 nm) to afford the title compound (0.564 g, 91%) as a yellow film.

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue was purified on silica gel (0-12%, MeOH/DCM, UV 220 nm)

Sources & evidence

ORD record
ord-71b6e8e6987448cb8ac490e4bfaeccf5
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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