Triphenylphosphine → HCID 66570330, compound

HRID 1727201Notes

Reaction equation

HRID 1727201 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[SH:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][N:49]=1>C1C=CC=CC=1>[N:49]1[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=1[S:47][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylateHCID 178418616HCID 178418616, compound

Product 1

HCID 66570330HCID 66570330, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of tert-butyl 3-(hydroxymethyl)-1-piperidinecarboxylate (Preparation 52, 1.0 g, 5 mmol) in benzene (40 ml) under nitrogen was added triphenyl phosphine (1.44 g, 5.5 mmol). Diethyl azodicarboxylate (0.86 ml, 5.5, mmol) in benzene (4 ml) was added dropwise and the reaction mixture was stirred for 5 min. 2-mercapto pyridine (0.61 g, 5.5 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture washed with sodium hydroxide (1M), water, and saturated brine. The organic extracts were dried (Na2SO4) and concentrated to an oil which was purified by flash chromatography on silica gel eluting with dichloromethane:ethyl acetate (9:1). The title compound was obtained as an oil (1.0 g, 65%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 h
  2. washThe reaction mixture washed with sodium hydroxide (1M), water, and saturated brine
  3. dry with materialThe organic extracts were dried (Na2SO4)
  4. concentrationconcentrated to an oil which
  5. customwas purified by flash chromatography on silica gel eluting with dichloromethane:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-3b8ddf76094b451ca83e9de2f37b035d
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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