(3R,4R)-pyrrolidine-3,4-diol → (3r,4r)-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-(3,4-dihydroxy-pyrrolidin-1-yl)-methanone

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O-:13])=O)[S:10][C:3]=12.[Li+].[NH:15]1[CH2:19][C@@H:18]([OH:20])[C@H:17]([OH:21])[CH2:16]1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:15]3[CH2:19][C@@H:18]([OH:20])[C@H:17]([OH:21])[CH2:16]3)=[O:13])[S:10][C:3]=12

Participants

Reactant 2

HCID 11499204(3R,4R)-pyrrolidine-3,4-diol

HCID 23677819Lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylate

Product 1

HCID 23595107(3r,4r)-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-(3,4-dihydroxy-pyrrolidin-1-yl)-methanone

Procedure

The title compound was prepared from lithium 7-chloro-thieno[3,2-b]pyridine-2-carboxylate and (3R,4R)-pyrrolidine-3,4-diol by a procedure analogous to Example 1C. MS: 299.3/301.3 (MH+); HPLC Rf: 3.091 min.; HPLC purity: 99%.

Sources & evidence

ORD record: ord-bd3c09a085ca4c718ec0b317f9362cc1
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995171B2

Reaction notes

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