Triphenylphosphine → HCID 59651884, compound

HRID 2042645Notes

Reaction equation

HRID 2042645 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:32][C:33]1[CH:38]=[C:37]([OH:39])[CH:36]=[CH:35][C:34]=1[C:40](=[O:42])[CH3:41].[C:43]([O:47][C:48]([N:50]1[CH2:55][CH2:54][CH:53](O)[CH2:52][CH2:51]1)=[O:49])([CH3:46])([CH3:45])[CH3:44]>O1CCCC1>[C:43]([O:47][C:48]([N:50]1[CH2:55][CH2:54][CH:53]([O:39][C:37]2[CH:36]=[CH:35][C:34]([C:40](=[O:42])[CH3:41])=[C:33]([F:32])[CH:38]=2)[CH2:52][CH2:51]1)=[O:49])([CH3:46])([CH3:44])[CH3:45]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 27249122'-Fluoro-4'-hydroxyacetophenone

Product 1

HCID 59651884HCID 59651884, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a 500 mL round bottom flask, diethyl azodicarboxylate (16.9 g, 97.3 mmol) and triphenylphosphine (25.5 g, 97.3 mmol) in tetrahydrofuran (200 mL) were cooled to 0° C. 1-(2-Fluoro-4-hydroxy-phenyl)-ethanone (10.0 g, 64.9 mmol) and 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (15.67 g, 77.9 mmol) in tetrahydrofuran (100 mL) were added. The reaction was warmed to ambient temperature 14 h. The solvents were concentrated under vacuum and methylene chloride (100 mL) and hexanes (500 mL) were added. The solids were filtered off. The mother liquor was concentrated under vacuum and chromatographed through silica gel with hexanes/ethyl acetate (7:3) as eluent to produce 17.5 g (80%). Mp 72-73° C.

Workup

  1. concentrationThe solvents were concentrated under vacuum and methylene chloride (100 mL) and hexanes (500 mL)
  2. additionwere added
  3. filtrationThe solids were filtered off
  4. concentrationThe mother liquor was concentrated under vacuum
  5. customchromatographed through silica gel with hexanes/ethyl acetate (7:3) as eluent
  6. customto produce 17.5 g (80%)

Sources & evidence

ORD record
ord-08f62f5e1182444fab07a6dd42023525
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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