Phenol → HCID 57234639, compound

HRID 341510Notes

Reaction equation

HRID 341510 reaction equation
[OH:1][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.[C:16]1(O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C>C1COCC1>[O:1]([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)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 57234639HCID 57234639, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-(hydroxymethyl)piperidine-1-carboxylate (0.300 g, 1.393 mmol), phenol (0.122 mL, 1.393 mmol), triphenylphosphine (0.440 g, 1.672 mmol) and N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide (0.390 g, 1.672 mmol) were combined in THF (4 mL) and stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure and purified by FCC (EtOAc: heptane, 1:1) to afford a white solid. This was further purified by trituration with diethyl ether to afford the title compound (0.289 g, 71%). Method B HPLC-MS: MH+ requires m/z=292 Found: m/z=235 (MH+-tBu), Rt=2.44 min (71%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by FCC (EtOAc: heptane, 1:1)
  3. customto afford a white solid
  4. customThis was further purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-b6405e247dd2463aa245e019d408cecc
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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