Cyclopropylamine → HCID 68616568, compound

HRID 1158411Notes

Reaction equation

HRID 1158411 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]([CH:33]2[CH2:35][CH2:34]2)[C:17](=[O:32])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:19]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:36]1([NH2:39])[CH2:38][CH2:37]1>>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]([CH2:15][N:16]([CH:33]2[CH2:35][CH2:34]2)[C:17](=[O:32])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:19]=2)[C@H:11]([CH2:13][NH:39][CH:36]2[CH2:38][CH2:37]2)[CH2:12]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 69828Cyclopropylamine2×HCID 86622395HCID 86622395, compound

Product 1

HCID 68616568HCID 68616568, compound

Procedure

In a similar manner as described in Example 149 for the reaction step D, the following starting material is prepared from (3R,4S)-3-({cyclopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.79 g, 3.65 mmol) (prepared according to example 9 using cyclopropyl amine instead of isopropyl amine under F), cyclopropyl amine (0.287 mL, 4.01 mmol) and NaBHOAc3 (1.14 g, 5.11 mmol) to give the title compound which is used in the next steps without further purification. TLC, Rf (CH2Cl2/AcOEt 9:1)=0.35. MS (LC-MS): 532.0 [M+H]+.

Workup

  1. customIn a similar manner as described in Example 149 for the reaction step D
  2. customprepared

Sources & evidence

ORD record
ord-3912e14d7261450499b6022f34c1f0cf
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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