Triphenylphosphine → HCID 68532453, compound

HRID 644208Notes

Reaction equation

HRID 644208 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([OH:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC([N:27]1[CH2:32][CH2:31][CH:30](O)[CH2:29][CH2:28]1)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([O:19][CH:30]2[CH2:31][CH2:32][NH:27][CH2:28][CH2:29]2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 11776TriphenylphosphineHCID 225489Methyl 4-(benzyloxy)-2-hydroxybenzoateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 68532453HCID 68532453, compound

Procedure

Using methods substantially equivalent to those described in Example 1-C, methyl 4-benzyloxy-2-hydroxybenzoate (2.0 g, 8.1 mmol), N-tert-butoxycarbonyl-4-hydroxy-piperidine (1.6 g, 8.1 mmol), triphenylphosphine (2.1 g, 8.1 mmol), and diethyl azodicarboxyalte (1.3 mL, 8.1 mmol) afforded, after purification by chromatography (SiO2: 5 to 15% EtOAc in hexanes), 2.57 g (74%) of the title compound.

Workup

  1. customafforded
  2. customafter purification by chromatography (SiO2: 5 to 15% EtOAc in hexanes), 2.57 g (74%) of the title compound

Sources & evidence

ORD record
ord-e600a6fec53d40f381972030ffe8d9c5
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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