Sodium Hydroxide → 1-(4-Fluoro-phenyl)-8-(8-methyl-naphthalen-1-ylmethyl)-1,3,8-triaza-spiro[4.5]-decan-4-one

HRID 729783Notes

Reaction equation

HRID 729783 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH:12]=O)=[CH:9][CH:8]=[CH:7]2.[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:25]3([CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[C:24](=[O:31])[NH:23][CH2:22]2)=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C(Cl)Cl.C(OCC)C.CC(O)=O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:25]3([CH2:26][CH2:27][N:28]([CH2:12][C:10]4[C:11]5[C:6](=[CH:5][CH:4]=[CH:3][C:2]=5[CH3:1])[CH:7]=[CH:8][CH:9]=4)[CH2:29][CH2:30]3)[C:24](=[O:31])[NH:23][CH2:22]2)=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 939151-(4-Fluorophenyl)-1,3,8-triazaspiro(4.5)decan-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 155634878-Methyl-1-naphthaldehyde

Product 1

HCID 220221991-(4-Fluoro-phenyl)-8-(8-methyl-naphthalen-1-ylmethyl)-1,3,8-triaza-spiro[4.5]-decan-4-one

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A 1-L 3-neck flask equipped with an overhead stirrer and a thermocouple was charged with 8-methyl-naphthalene-1-carbaldehyde (13.75 g, 0.08 mol) and 1-(4-fluoro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one (21.5 g, 0.085 mol) under N2 in CH2Cl2 (500 mL). After stirring for 20 min, HOAc (1 mL) was added followed by careful addition of solid NaBH(OAc)3 (33.4 g, 0.157 mol). The mixture was stirred for 16 h at room temperature (suspension becomes a solution). The reaction was then warmed at 50° C. for 2 h, cooled down to room temperature and then treated with 0.5 N NaOH (50 mL), stirred for 10 min and then diluted with CH2Cl2 (100 mL). The organic layer was isolated and dried over MgSO4. The solvent was evaporated to yield a residue, which was suspended in diethyl ether, stirred for 20 min, filtered and dried in a 60° C. vacuum oven to yield 1-(4-fluoro-phenyl)-8-(8-methyl-naphthalen-1-ylmethyl)-1,3,8-triaza-spiro[4.5]-decan-4-one as a white solid;

Workup

  1. customA 1-L 3-neck flask equipped with an overhead stirrer
  2. stirringThe mixture was stirred for 16 h at room temperature (suspension
  3. temperaturecooled down to room temperature
  4. stirringstirred for 10 min
  5. customThe organic layer was isolated
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated
  8. customto yield a residue, which
  9. stirringstirred for 20 min
  10. filtrationfiltered
  11. customdried in a 60° C. vacuum oven

Sources & evidence

ORD record
ord-c3673eac36fb42e18e79a4f40370ea80
Source dataset
uspto-grants-2009_09
Patent number
US07582649B2

Reaction notes

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