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

HRID 1824961Notes

Reaction equation

HRID 1824961 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5](Br)[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.[C:15]([O:19][C:20]([N@@:22]1[CH2:24][CH:23]1[CH3:25])=[O:21])([CH3:18])([CH3:17])[CH3:16]>>[C:15]([O:19][C:20]([NH:22][C@H:23]([CH3:25])[CH2:24][C:5]1[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 10942718Tert-butyl 2-methylaziridine-1-carboxylateHCID 221448715-Trifluoromethyl-7-bromobenzofuran

Product 1

HCID 23573467(R)-N-tert-butoxycarbonyl 1-(5-trifluoromethylbenzofur-7-yl)-2-aminopropaneYield 24.9%

Procedure

Beginning with 0.256 gm (0.97 mMol) 5-trifluoromethyl-7-bromobenzofuran and 0.142 gm (0.90 mMol) (R)-(−)-N-tert-butoxycarbon-yl-2-methylaziridine, 0.077 gm (23%) of the desired compound were prepared essentially as described in Example 10.

Sources & evidence

ORD record
ord-caece74d57994e2bbb2a4db3d7a3dd7a
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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