Tetrahydrofuran → HCID 86621491, compound

HRID 1726700Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@@H:23]([C:34]([O:36][CH3:37])=[O:35])[CH2:22]1.[N:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1.O1CCCC1.N(C(OCC)=O)=NC(OCC)=O>>[N:38]1[CH:43]=[CH:42][C:41]([O:20][C@@H:21]2[CH2:26][CH2:25][C@H:24]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[C@@H:23]([C:34]([O:36][CH3:37])=[O:35])[CH2:22]2)=[CH:40][CH:39]=1

Participants

Reactant 5

HCID 8028Tetrahydrofuran2×

HCID 11776Triphenylphosphine

HCID 220568ethyl N-ethoxycarbonyliminocarbamate

HCID 86621492HCID 86621492, compound

HCID 178418642HCID 178418642, compound

Product 1

HCID 86621491HCID 86621491, compound

Procedure

Triphenylphosphine (2.0E3 mg, 0.0077 mol) was added to a solution of 1-tert-butyl 2-methyl (1S,2S,4S)-4-hydroxycyclohexane-1,2-dicarboxylate (1.0 g, 0.0039 mol) and 4-pyridinol (730 mg, 0.0076 mol) in tetrahydrofuran (10.0 mL, 0.123 mol) at rt. A solution of diethyl azodicarboxylate (1200 uL, 0.0077 mol) in tetrahydrofuran (10.0 mL, 0.123 mol) was added. The reaction mixture was stirred at rt overnight. The reaction was chromatographed by combiflash (ethyl acetate in hexanes: 80%) to give 1-tert-butyl 2-methyl(1S,2S,4R)-4-(pyridin-4-yloxy)cyclohexane-1,2-dicarboxylate, contaminated with a little Ph3PO, which was used in next step.

Workup

customThe reaction was chromatographed by combiflash (ethyl acetate in hexanes: 80%)

Sources & evidence

ORD record: ord-6854764b69a14985966dd95db78021c8
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491724B2

Reaction notes

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