Tetrahydrofuran → 1-Tert-butyl 3-methyl (2s,3s,5s)-2-[(4-phenyl-3,6-dihydropyridin-1(2h)-yl)carbonyl]-5-(pyridin-4-yloxy)piperidine-1,3-dicarboxylate

HRID 61446Notes

Reaction equation

HRID 61446 reaction equation
[OH:1][C@H:2]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:5]([C:15]([N:17]2[CH2:22][CH:21]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[O:16])[C@@H:4]([C:29]([O:31][CH3:32])=[O:30])[CH2:3]1.O1CCCC1.[N:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C:23]1([C:20]2[CH2:21][CH2:22][N:17]([C:15]([C@@H:5]3[C@@H:4]([C:29]([O:31][CH3:32])=[O:30])[CH2:3][C@H:2]([O:1][C:41]4[CH:42]=[CH:43][N:38]=[CH:39][CH:40]=4)[CH2:7][N:6]3[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:16])[CH2:18][CH:19]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 696399861-tert-butyl 3-methyl (2S,3S,5R)-5-hydroxy-2-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]piperidine-1,3-dicarboxylateHCID 178418642HCID 178418642, compound

Product 1

HCID 1317319271-Tert-butyl 3-methyl (2s,3s,5s)-2-[(4-phenyl-3,6-dihydropyridin-1(2h)-yl)carbonyl]-5-(pyridin-4-yloxy)piperidine-1,3-dicarboxylate

Conditions

Temperature
70 °C

Procedure

To a solution of 1-tert-butyl 3-methyl(2S,3S,5R)-5-hydroxy-2-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]piperidine-1,3-dicarboxylate (100 mg, 0.0002 mol) in tetrahydrofuran (0.912 mL, 0.0112 mol) was added 4-pyridinol (25.7 mg, 0.000270 mol), triphenylphosphine (70.8 mg, 0.000270 mol), followed by diisopropyl azodicarboxylate (0.0532 mL, 0.000270 mol). The mixture was heated at 70 Celsius overnight. After concentrated to dry, the mixture was purified on silica gel, eluting with 0 to 40% EtOAc in hexane, to afford the desired ether compound (56 mg, 50%). MS (ESI): (M+H)+=522.1.

Workup

  1. concentrationAfter concentrated
  2. customto dry
  3. customthe mixture was purified on silica gel
  4. washeluting with 0 to 40% EtOAc in hexane
  5. customto afford the desired ether compound (56 mg, 50%)

Sources & evidence

ORD record
ord-a1cd006ab8e6436f97232131ca082e55
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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