Tetrahydrofuran → HCID 86621491, compound

HRID 535106Notes

Reaction equation

HRID 535106 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

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86621492HCID 86621492, compoundHCID 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

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

Sources & evidence

ORD record
ord-d6ac833cf7b24b14ac62aa3bc0eb11a2
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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