Tert-butyl 2-methylaziridine-1-carboxylate → (R)-N-tert-butoxycarbonyl 1-(5-fluorobenzofur-7-yl)-2-aminopropane

HRID 1824947Notes

Reaction equation

HRID 1824947 reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[C:12]([O:16][C:17]([N@@:19]1[CH2:21][CH:20]1[CH3:22])=[O:18])([CH3:15])([CH3:14])[CH3:13]>>[C:12]([O:16][C:17]([NH:19][C@H:20]([CH3:22])[CH2:21][C:4]1[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=[C:2]([F:1])[CH:3]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

3

Reactant 2

HCID 10942718Tert-butyl 2-methylaziridine-1-carboxylateHCID 221448167-Bromo-5-fluoro-1-benzofuran

Product 1

HCID 23573466(R)-N-tert-butoxycarbonyl 1-(5-fluorobenzofur-7-yl)-2-aminopropaneYield 44.3%

Procedure

Beginning with 5.7 gm (26.6 mMol) 5-fluoro-7-bromobenzofuran and 3.9 gm (24.8 mMol) (R)-(−)-N-tert-butoxycarbonyl-2-methylaziridine, 3.22 gm (44%) of the desired compound were prepared essentially as described in Example 10.

Sources & evidence

ORD record
ord-0631ffbb227d4e469e91a05eb46301c5
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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