Triphenylphosphine → HCID 86622728, compound

HRID 2410327Notes

Reaction equation

HRID 2410327 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:15]([O:22][C:23]1[C:28]2[C:29]([OH:32])=[N:30][O:31][C:27]=2[CH:26]=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O[CH2:34][CH2:35][CH:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:15]([O:22][C:23]1[C:28]2[C:29]([O:32][CH2:34][CH2:35][CH:36]3[CH2:37][CH2:38][N:39]([C:42]([O:44][C:45]([CH3:46])([CH3:48])[CH3:47])=[O:43])[CH2:40][CH2:41]3)=[N:30][O:31][C:27]=2[CH:26]=[CH:25][CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 178518986HCID 178518986, compound

Product 1

HCID 86622728HCID 86622728, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diisopropyl azodicarboxylate (3.2 mL, 17 mmol) was added to a mixture of 4-(benzyloxy)-1,2-benzisoxazol-3-ol (2.7 g, 11 mmol, EXAMPLE 7, Step 1), tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (3.1 g, 14 mmol), and triphenylphosphine (4.3 g, 17 mmol) in toluene (11 mL) at 0° C. The mixture was stirred at room temperature for 16 h, and concentrated in vacuo to give a yellow oil. The residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 4:1) to give 3.8 g (76%) of the title compound as a colorless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a yellow oil
  3. customThe residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-2c58a458370a4e4abe46bb4b99dc55be
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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