1,2-Dichloroethane → HCID 57194245, compound

HRID 496640Notes

Reaction equation

HRID 496640 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][NH:19][O:20][CH3:21].C(Cl)CCl>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[C@H:9]1[C:14](=[O:16])[N:19]([O:20][CH3:21])[CH3:18])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 14037017(2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 57194245HCID 57194245, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of compound 64 (8.42 g), N,O-dimethyl hydroxylamine HCl (10.66 g), DMAP (26.69 g), and EDC (10.47 g) in dichloromethane (500 ml) was stirred at ambient temperature for 16 hours. The reaction mixture was then applied directly to a silica flash column and eluted with ethyl acetate to give (2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxy-2-(N-methoxy-N-methylcarbamoyl)pyrrolidine (compound 65) as a clear gum(7.6 g).

Workup

  1. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-8e6da7377adb44b1911779e162c0a580
Source dataset
uspto-grants-2005_09
Patent number
US06946468B1

Reaction notes

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