4-Methylmorpholine → 1,1-Dimethylethyl (2S)-2-[(methoxymethylamino)carbonyl]-1-pyrrolidinecarboxylate

HRID 1821568Notes

Reaction equation

[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:17][NH:18][O:19][CH3:20].CN1CCOCC1>>[N:8]1([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([N:18]([O:19][CH3:20])[CH3:17])=[O:12]

Participants

Reactant 3

HCID 79724-Methylmorpholine

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Product 1

HCID 6882981,1-Dimethylethyl (2S)-2-[(methoxymethylamino)carbonyl]-1-pyrrolidinecarboxylate

Procedure

Boc-Proline (2.00 g, 9.29 mmol) and N,O-Dimethylhydroxylaminehydrochloride (0.91 g, 9.29 mmol) were treated as described for 1 using NMM (2 ml, 18.4 mmol) and CAIBE (1.47 ml, 9.29 mmol).

Sources & evidence

ORD record: ord-883185de49d24f678c08eca91d261b18
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608577B2

Reaction notes

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