Cyclopropanecarboxaldehyde → Ammonia

HRID 1244856Notes

Reaction equation

HRID 1244856 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[CH:14]1([CH:17]=O)[CH2:16][CH2:15]1>>[NH3:1].[CH:14]1([CH2:17][NH:1][C@H:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 123114CyclopropanecarboxaldehydeHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Product 2

HCID 222AmmoniaHCID 58718606887767-14-8

Procedure

tert-butyl (3S)-3-(cyclopropylmethylamino)pyrrolidine-1-carboxylate was prepared by a method similar to that described in preparation 1 using tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate and cyclopropane carboxaldehyde except that the crude product was purified by chromatography on silica gel eluting with a solvent gradient of dichloromethane changing to dichloromethane:methanol:0.88 ammonia (90:10:1 by volume) to yield the title compound, 5.2 g (81%).

Workup

  1. customtert-butyl (3S)-3-(cyclopropylmethylamino)pyrrolidine-1-carboxylate was prepared by a method similar to
  2. customwas purified by chromatography on silica gel eluting with a solvent gradient of dichloromethane changing to dichloromethane

Sources & evidence

ORD record
ord-d1783ced332b46c49373e0cfe287734c
Source dataset
uspto-grants-2006_10
Patent number
US07122683B2

Reaction notes

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