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Methanol → HCID 12709713, compound

HRID 1018635
Notes
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Reaction equation

HRID 1018635 reaction equation
FC(F)(F)[C:3]1[CH:4]=[C:5]([CH:26]=[C:27](C(F)(F)F)[CH:28]=1)[C:6]([N:8]1[CH2:25][CH2:24][C:11]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[CH:12]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=O.[C:35]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:6]([N:8]1[CH2:9][CH2:10][C:11]2([C:15](=[O:16])[N:14]([CH3:35])[C:13](=[O:17])[CH:12]2[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:24][CH2:25]1)[C:5]1[CH:26]=[CH:27][CH:28]=[CH:3][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 59872176HCID 59872176, compound

Product 1

HCID 12709713HCID 12709713, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

(rac)-8-Benzyl-4-phenyl-2,8-diaza-spiro[4.5]decane-1,3-dion (3.0 g, 9.0 mmol, synthesis described in example 156) was dissolved in dry tetrahydrofuran (50 mL) and triphenylphosphin (3.1 g, 11.7 mmol), methanol (0.374 g, 11.7 mmol) and diethylazodicarboxylate (5.35 mL, 40% in toluene, 11.7 mmol) were added sequentially and stirred at room temperature overnight. The solvent was evaporated and the residue was purified by chromatography on silica gel (dichloromethane/methanol/triethyl amine 98:1:1) to yield the intermediate (rac)-8-benzyl-2-methyl-4-phenyl-2,8-diaza-spiro[4.5]decane-1,3-dion (2.57 g, 82%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography on silica gel (dichloromethane/methanol/triethyl amine 98:1:1)

Sources & evidence

ORD record
ord-a1902f806b0648f2a5fd6ab39cf100bc
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06482829B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes