3-Cyanophenol → HCID 22857710, compound

HRID 2259204Notes

Reaction equation

HRID 2259204 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]([C:17]1[CH:18]=[C:19](O)[CH:20]=[CH:21][CH:22]=1)#[N:16].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([C:15]#[N:16])[CH:22]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 133943-CyanophenolHCID 643448(S)-(-)-N-Boc-prolinolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22857710HCID 22857710, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.5 g (20 mmol) sample of (S)-1-BOC-2-pyrrolidinemethanol (from Example 1a) and 3.57 g (30 mmol) of 3-cyanophenol (Aldrich) were added to a complex of TPP and DEAD, (prepared as in Example 5b above, 30 mmol of each) in 100 mL of THF. The reaction was stirred for 16 hr, the solvents were removed under vacuum, and the residue was extracted with hexane and chromatographed on silica gel, eluting with 100:0-85:15 hexane:ethyl acetate to give 2.71 g of the title compound. MS: 303 (M+H)+, 320 (M+NH4)+. NMR (CDCl3) δ: 1.48 (s, 9H), 1.84-2.05 (m, 4H), 3.35-3.45 (br, 2H), 3.75-3.95 (m, 1H), 4.05-4.18 (br, 2H), 7.25-7.40 (m, 4H).

Workup

  1. customthe solvents were removed under vacuum
  2. extractionthe residue was extracted with hexane
  3. customchromatographed on silica gel
  4. washeluting with 100:0-85:15 hexane

Sources & evidence

ORD record
ord-217b005dd5564c9b976c13f7e943d86c
Source dataset
uspto-grants-1995_12
Patent number
US05472958

Reaction notes

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