Cyclopropylamine → HCID 68616132, compound

HRID 1158400Notes

Reaction equation

HRID 1158400 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH:13]=O)[C@H:10]([CH2:15][N:16]([C:20](=[O:34])[C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:22]=2)[CH:17]([CH3:19])[CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:35]1([NH2:38])[CH2:37][CH2:36]1>CCOC(C)=O.CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:38][CH:35]2[CH2:37][CH2:36]2)[C@H:10]([CH2:15][N:16]([C:20](=[O:34])[C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([O:28][CH2:29][CH2:30][CH2:31][O:32][CH3:33])[CH:22]=2)[CH:17]([CH3:18])[CH3:19])[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 86622392HCID 86622392, compound

Product 1

HCID 68616132HCID 68616132, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

From (3R,4S)-3-({[4-methyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (3 g, 6.29 mmol), cyclopropyl amine (0.395 mL, 6.92 mmol) and NaBHOAc3 (1.87 g, 8.81 mmol) and purification by flash chromatography on silica gel (AcOEt/MeOH 100:0 to 85:15) to give the title compound as colorless oil. TLC, Rf (AcOEt)=0.63. MS (LC-MS): 518.3 [M+H]+; tR (HPLC, Nucleosil C-18HD (4×70 mm, 3 μm), 20-100% CH3CN/H2O/6 min, 100% CH3CN/1.5 min; flow: 1 mL/min): 5.37 min.

Sources & evidence

ORD record
ord-f6d8fec1e1ad48489b05bfd6eb90bddc
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

Loading…