Toluene → HCID 59651926, compound

HRID 2042589Notes

Reaction equation

HRID 2042589 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC[O:22]C(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1.[OH:39][CH:40]1[CH2:45][CH2:44][N:43]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:42][CH2:41]1.[CH2:53]([O:55][C:56](=[O:68])[C:57](=O)[CH2:58][CH2:59][C:60]1[CH:65]=[CH:64][C:63](O)=[CH:62][CH:61]=1)[CH3:54]>C1COCC1>[C:49]([O:48][C:46]([N:43]1[CH2:42][CH2:41][CH:40]([O:39][C:63]2[CH:64]=[CH:65][C:60]([C:59](=[O:22])[CH2:58][CH2:57][C:56]([O:55][CH2:53][CH3:54])=[O:68])=[CH:61][CH:62]=2)[CH2:45][CH2:44]1)=[O:47])([CH3:52])([CH3:51])[CH3:50]

Participants

7

Reactant 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 20193455HCID 20193455, compound

Product 1

HCID 59651926HCID 59651926, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To triphenylphosphine (2.48 g, 9.48 mmol) in THF (25 mL) was added 40% w/w DEAD in toluene (4.00 mL, 8.95 mmol) and the reaction was cooled at 0° C. before adding a mixture of 4-hydroxy-boc-piperidine (1.44, 7.14 mmol) and 4-(4-hydroxyphenyl)-oxo-butyric acid ethyl ester (1.3 g, 5.8 mmol) in THF (25 mL). After overnight stirring at r.t., the reaction was concentrated and the product was purified using a Single Step column (7:3 hexanes:ethyl acetate) to obtain 2.17 g (91%); MS m/z 406 (M+H).

Workup

  1. additionbefore adding
  2. concentrationthe reaction was concentrated
  3. customthe product was purified
  4. customto obtain 2.17 g (91%)

Sources & evidence

ORD record
ord-392c2af5919c4c899455b708ca1f7d8c
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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