4-Chlorophenol → HCID 21906062, compound

HRID 1990908Notes

Reaction equation

HRID 1990908 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([OH:28])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[Cl:29][C:30]1[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CCOCC>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:33]2[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 21906062HCID 21906062, compoundYield 125.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of DIAD (11.4 mL; 55.0 mmol) in THF (15 mL) was added dropwise over 35 min to an ice-cold solution of 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (10.06 g; 50.0 mmol), 4-chlorophenol (5.1 mL; 50.4 mmol) and triphenylphosphine (14.44 g; 55.1 mmol) in THF (40 mL). After 2.9 days at room temperature the solvent was removed on a rotary evaporator leaving a viscous liquid; hexanes was added then evaporated leaving a solid. Ether (25 mL), followed by hexanes (100 mL), was added and the solid was filtered and washed with hexanes. The filtrate was concentrated on a rotary evaporator leaving a golden, viscous liquid (19.6 g). The crude product was used as is. ESIMS 311.9/313.8 (25/10) [MH+], 296.9/298.8 (100/34) [MH+—C4H9+CH3CN], 255.9/257.8 (94/32) [MH+—C4H9], 212.0/214.0 (13/5) [MH+—C4H9—CO2].

Workup

  1. customAfter 2.9 days at room temperature the solvent was removed on a rotary evaporator
  2. customleaving a viscous liquid
  3. customthen evaporated
  4. customleaving a solid
  5. additionwas added
  6. filtrationthe solid was filtered
  7. washwashed with hexanes
  8. concentrationThe filtrate was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-b998da39cf5847e592123e497529a9a9
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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