Triphenylphosphine → HCID 66570329, compound

HRID 1727198Notes

Reaction equation

HRID 1727198 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][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][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 178418616HCID 178418616, compound

Product 1

HCID 66570329HCID 66570329, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of tert-butyl 4-(hydroxymethyl)-1-piperidinecarboxylate (Preparation 48, 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 (0.7 g, 58%).

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-17bae28a1e2a46239b0a977d6823b0bf
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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