Phosgene → (R)-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboxylic Acid Tert-Butyl Ester

HRID 496664Notes

Reaction equation

HRID 496664 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10](NC2C=CC=CC=2N)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:24]([CH2:27][CH3:28])CC.[C:29](Cl)(Cl)=[O:30]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]1[N:24]1[C:27]2[CH:28]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:8][C:29]1=[O:30])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 59918925(R)-3-(2-Aminophenylamino)piperidine-1-carboxylic acid tertbutyl ester

Product 1

HCID 69800710(R)-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboxylic Acid Tert-Butyl EsterYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3(R)-(2-Amino-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (52 mg, 0.18 mmol), Et3N (1.0 ml) in CH2Cl2 (1 ml) at 0° C. was added a solution of phosgene (20% in toluene, 0.1 ml). After stirring for 2 hr and evaporation of solvent, the residue was purified by chromatography (1%-2% MeOH in CH2Cl2) to give a colorless oil (34 mg, 60%). 1H-NMR (300 MHz, CDCl3) δ 7.80 (d, 1H), 4.20 (m, 3H), 3.50 (m, 1H), 2.75 (m, 1H), 2.65 (m, 1H), 2.10 (m, 1H), 1.90 (m, 1H), 1.70 (m, 1H), 1.50 (s, 9H) ppm; IR (film) 3067, 2975, 2935, 2858, 1745, 1692, 1612, 1487, 1423, 1383, 1347, 1266, 1246, 1158 cm−1; LRMS (calculated for C17H23N3O3—BOC)+ 217. found 217.

Workup

  1. customevaporation of solvent
  2. customthe residue was purified by chromatography (1%-2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-0b502b3d1f144626bb15bc8d5ae371b4
Source dataset
uspto-grants-2005_09
Patent number
US06946477B2

Reaction notes

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