Methylamine → HCID 68617139, compound

HRID 1158391Notes

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:35])[C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH3:28])=[C:23]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])[CH:22]=2)[CH:17]([CH3:19])[CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:36][NH2:37].[BH4-].[Na+].C(Cl)Cl.CO.[NH4+].[OH-]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:37][CH3:36])[C@H:10]([CH2:15][N:16]([C:20](=[O:35])[C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH3:28])=[C:23]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH3:34])[CH:22]=2)[CH:17]([CH3:19])[CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 6329Methylamine

HCID 4311764Sodium borohydride

HCID 21896990Dichloromethane methanol ammonium hydroxide

HCID 86622389HCID 86622389, compound

Product 1

HCID 68617139HCID 68617139, compound

Procedure

In a similar manner as described in Example 9 for the reaction step J, the following starting materials is prepared from (3R,4S)-3-({[4-ethyl-3-(3-methoxy-propoxy)-benzoyl]-isopropyl-amino}-methyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (3.5 g, 6 mmol), methyl amine (0.93 mL, 30 mmol) and NaBH4 (0.454 g, 12 mmol) and purification by flash chromatography on silica gel (CH2Cl2/MeOH 1:1) to (CH2Cl2/MeOH/NH4OH 89:10:1) to give the title compound as colorless oil. TLC, Rf (CH2Cl2/MeOH/NH4OH 89:10:1)=0.29. MS (LC-MS): 506.2 [M+H]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 5.38 min.

Workup

customIn a similar manner as described in Example 9 for the reaction step J

Sources & evidence

ORD record: ord-cf4d73f956284bfca7138909cf4dab7e
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807709B2

Reaction notes

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