Bromomethylcyclopropane → (4R,9aR)-6-(1-(RS)-Cyclopropylmethoxy-butyl)-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene

HRID 11959Notes

Reaction equation

C(OC([N:8]1[CH2:20][CH:19]([CH3:21])[N:18]2[CH:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([CH:22]([OH:26])[CH2:23][CH2:24][CH3:25])=[CH:14][CH:13]=3)[CH2:9]1)=O)(C)(C)C.[CH:27]1([CH2:30]Br)[CH2:29][CH2:28]1>>[CH:27]1([CH2:30][O:26][CH:22]([C:15]2[N:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[CH2:11][C@H:10]2[N:18]3[C@H:19]([CH3:21])[CH2:20][NH:8][CH2:9]2)[CH2:23][CH2:24][CH3:25])[CH2:29][CH2:28]1

Participants

Reactant 2

HCID 81503Bromomethylcyclopropane

HCID 695573066-(1-hydroxy-butyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

HCID 69556436(4R,9aR)-6-(1-(RS)-Cyclopropylmethoxy-butyl)-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene

Procedure

(4R,9aR)-6-(1-(RS)-Cyclopropylmethoxy-butyl)-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene di-trifluoroacetate (53 mg) was made from 6-(1-hydroxy-butyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (54 mg), using cyclopropylmethyl bromide (29 μl) in place of methyl iodide, according to the procedure described in Example 63 to afford the product as a colorless oil: HPLC [Xterra; 50/80; 255 nm] 99.6%, 2.29 min; MS (ES) 316.4 (MH+).

Sources & evidence

ORD record: ord-764f9b0f47cd41078ba8f211eade6ec3
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098337B2

Reaction notes

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