Triphenylphosphine → tert-Butyl 5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylate

HRID 1016175Notes

Reaction equation

HRID 1016175 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:21])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[C:4]([CH2:22]O)[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:8]1([CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:12][CH2:13]1)[O:21][CH2:22]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 57889172tert-Butyl 4-(4-chloro-2-(hydroxymethyl)phenyl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 57889918tert-Butyl 5-chloro-3H-spiro[isobenzofuran-1,4'-piperidine]-1'-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 4-(4-chloro-2-(hydroxymethyl)phenyl)-4-hydroxypiperidine-1-carboxylate (1.3 g, 3.80 mmol) and triphenylphosphine (1.496 g, 5.70 mmol) in THF (20 mL) was treated with DEAD (0.903 mL, 5.70 mmol), and the mixture was stirred overnight at room temperature. The mixture was concentrated in-vacuo, and the residue was purified over silica gel, eluting with ethyl acetate/hexanes (5%-25% ethyl acetate), to yield the title compound (1.19 g, 3.67 mmol, 97% yield) as a colorless oil.

Workup

  1. concentrationThe mixture was concentrated in-vacuo
  2. customthe residue was purified over silica gel
  3. washeluting with ethyl acetate/hexanes (5%-25% ethyl acetate)

Sources & evidence

ORD record
ord-a56ee0c523f8438f85ccac826c4f87e5
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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