Triphenylphosphine → HCID 18474280, compound

HRID 651527Notes

Reaction equation

HRID 651527 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][CH:46]([CH2:49]O)[CH2:45][CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37].N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:49][CH:46]2[CH2:47][CH2:48][N:43]([C:41]([O:40][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:42])[CH2:44][CH2:45]2)[CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 18474284HCID 18474284, compound

Product 1

HCID 18474280HCID 18474280, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 272 mg (0.809 mmol) of 3-[(2-chlorophenoxy) methyl]phenol, as prepared in the preceding step, in methylene chloride (5 mL) containing 275 mg (1.05 mmol) of triphenylphosphine and 208 mg (0.97 mmol) of N-(tert-butoxycarbonyl)-4-piperidinemethanol, as prepared in step (b) of Example 1, was added slowly 165 μL (1.04 mmol) of diethyl azodicarboxylate. The reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was quenched with water, extracted into diethyl ether, dried (MgSO4), and flash chromatographed (hexane/ethyl acetate (1:4 to 1:2)) to give 221 mg (58% yield) of the title compound as a colorless oil. 1H-NMR (300 MHz, CDCl3) δ 7.38 (dd, 1 H, J=1.5, 7.8 Hz), 7.28 (t, 1 H, J=8.1 Hz), 7.15-7.21 (m, 1 H), 8.82-7.03 (m, 5 H), 5.13 (s, 2 H), 3.82 (d, 2 H, J=6.4 Hz), 2.74 (t, 2 H), 1.91-2.00 (m, 1 H), 1.84 (d, 2 H), and 1.47 (s, 9 H). Mass spectrum (MALDI-TOF; α-cyano-4-hydroxycinnamic acid matrix) calcd. for C24H30ClNO4S: 454.2 (M+Na). Found: 454.4.

Workup

  1. customas prepared in step (b) of Example 1
  2. customThe reaction mixture was quenched with water
  3. extractionextracted into diethyl ether
  4. dry with materialdried (MgSO4), and flash
  5. customchromatographed (hexane/ethyl acetate (1:4 to 1:2))

Sources & evidence

ORD record
ord-4b1708f59a9b494eba8970668392630b
Source dataset
uspto-grants-2001_08
Patent number
US06281206B1

Reaction notes

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