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 535055Notes

Reaction equation

HRID 535055 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-48d76b595c324eb28704083785c07a86
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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