Sodium hydride → 8-(Benzyloxy)-1,4-dioxaspiro[4.5]decane
Reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Na+].F[C:15](F)(F)[C:16]1[CH:17]=[C:18](CBr)[CH:19]=[CH:20][CH:21]=1>>[C:16]1([CH2:15][O:11][CH:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1Participants
4
Procedure
When the bridging group n is --OCH2 --, 1,4-dioxaspiro[4.5]decan-8-ol (the preparation of which was previously described) is treated with sodium hydride and reacted with an appropriately substituted or unsubstituted phenylmethyl bromide, for example, 3-trifluoromethylphenylmethyl bromide, affording the corresponding 8-phenylmethoxy-1,4-dioxaspiro[4.5]decane. The 1,4-dioxaspiro functional group is then cleaved from the so-prepared molecule with acetic acid and water, affording the corresponding 4-phenylmethoxycyclohexanone, which is in turn reacted with cyanoguanidine, yielding the targeted 2,4-diamino-6-phenylmethoxy-5,6,7,8-tetrahydroquinazoline. Example 11 provides a detailed description of how this reaction is conducted.
Sources & evidence
- ORD record
- ord-1964a58fdb33476b9cb2731ea9fee11b
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05536725
Reaction notes
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