Hydrogen Peroxide → HCID 22799507, compound

HRID 2072463Notes

Reaction equation

HRID 2072463 reaction equation
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([CH2:17][CH:18]4[CH2:27][CH2:26][C:25]5[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH3:29])[CH:24]=5)[C:19]4=[O:30])[CH2:13][CH2:12]3)[C:10](=[O:31])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[OH-].[Na+].OO.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([CH2:17][C@H:18]4[CH2:27][CH2:26][C:25]5[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH3:29])[CH:24]=5)[C@H:19]4[OH:30])[CH2:13][CH2:12]3)[C:10](=[O:31])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 21408205HCID 21408205, compound

Product 1

HCID 22799507HCID 22799507, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1-Phenyl-8-[(1,2,3,4-tetrahydro-6-methoxy-1-oxo-2-naphthalenyl)methyl]-1,3,8-triazaspiro[4.5]decan-4-one (5.4 g) dissolved in 60 ml of dry tetrahydrofuran is added dropwise to a flask charged with 2.1 equivalents of a 1 molar tetrahydrofuran solution of lithium tri-sec-butylborohydride which has been cooled to -78° C under an argon atmosphere. The resulting solution is stirred for 16 hours at room temperature. The reaction mixture is treated at 0° C with 15 ml of 3 molar sodium hydroxide followed by the addition of 15 ml of 30% hydrogen peroxide. The aqueous phase is saturated with potassium carbonate and the organic layer is separated and concentrated. The residue is dissolved in methylene chloride, washed with water, dried and concentrated producing the crude product. Two crystallizations of this material from absolute ethanol/methylene chloride yield 3.8 g of isomerically pure title compound, melting point 182°-183° C.

Workup

  1. additionis added dropwise to a flask
  2. customthe organic layer is separated
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in methylene chloride
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0a69ef7fd1dc452fa8f864fc7d3f3262
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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