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Cyclohexanol → HCID 66722447, compound

HRID 1044381
Notes
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Reaction equation

HRID 1044381 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[O:13]=[C:14]1[NH:18][C:17](=[O:19])[C:16]2([CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]2)[NH:15]1.[CH:32]1(O)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>>[CH:32]1([N:18]2[C:17](=[O:19])[C:16]3([CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]3)[NH:15][C:14]2=[O:13])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 7966CyclohexanolHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 42614218Tert-butyl 2,4-dioxo-1,3,7-triazaspiro[4.5]decane-7-carboxylate

Product 1

HCID 66722447HCID 66722447, compound

Procedure

Diethyl azodicarboxylate (0.315 mL, 0.00200 mol) was added to a mixture of tert-butyl 2,4-dioxo-1,3,7-triazaspiro[4.5]decane-7-carboxylate (269.3 mg, 0.001000 mol), cyclohexanol (0.156 mL, 0.00150 mol), and triphenylphosphine (524 mg, 0.00200 mol) in tetrahydrofuran (6 mL, 0.08 mol). The reaction mixture was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by Combiflash with ethyl acetate/hexane. LC-MS: 296.2 (M−Bu+2H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by Combiflash with ethyl acetate/hexane

Sources & evidence

ORD record
ord-579d9fece6a041eba90c3fcac71afea3
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08563570B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes