3-Hydroxyazetidine → (2S)-1-({1-[4-(dimethylamino)butanoyl]-4-methylene-2-pyrrolidinyl}carbonyl)-3-azetidinol

HRID 1349060Notes

Reaction equation

C(O[C:6]([N:8]1[CH2:15][C:14](=[CH2:16])[CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])(C)(C)C.[CH3:17][N:18]([CH3:25])[CH2:19][CH2:20][CH2:21]C(Cl)=O.[NH:26]1[CH2:29][CH:28]([OH:30])[CH2:27]1>>[CH3:25][N:18]([CH3:17])[CH2:19][CH2:20][CH2:21][C:6]([N:8]1[CH2:15][C:14](=[CH2:16])[CH2:13][C@H:9]1[C:10]([N:26]1[CH2:29][CH:28]([OH:30])[CH2:27]1)=[O:12])=[O:7]

Participants

Reactant 3

HCID 15142903-Hydroxyazetidine

HCID 150876904-(Dimethylamino)butanoyl chloride

HCID 21727417(2S)-1-((tert-butoxy)carbonyl)-4-methylidenepyrrolidine-2-carboxylic acid

Product 1

HCID 69252460(2S)-1-({1-[4-(dimethylamino)butanoyl]-4-methylene-2-pyrrolidinyl}carbonyl)-3-azetidinol

Procedure

Following the general method as outlined in Example 22, starting from 1-(tert-butoxycarbonyl)-4-methyleneproline, 4-(dimethylamino)butanoyl chloride, and 3-azetidinol the title compound was obtained in 100% purity by LC/MS. MS(ESI+): m/z=296.4.

Sources & evidence

ORD record: ord-e1d5754aebc0423fb9891354838e1ffb
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211601B2

Reaction notes

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