HCID 68160224, compound → HCID 68160870, compound

HRID 537351Notes

Reaction equation

HRID 537351 reaction equation
[C:1]([C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2/[CH:22]=[CH:23]/[C:24]([O:26][CH2:27][CH3:28])=[O:25])[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)#[N:2]>CO>[C:1]([C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]1)#[N:2]

Participants

3

Reactant 1

HCID 68160224HCID 68160224, compound

Product 1

HCID 68160870HCID 68160870, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

(E)-tert-butyl 4-cyano-4-(2-(3-ethoxy-3-oxoprop-1-enyl)phenyl)piperidine-1-carboxylate (21, 278 mg, 0.72 mmol) was dissolved in MeOH (7 mL). The solution was degassed with Ar for 2 min. Pd/C (10%, 30 mg) was added and H2 was bubbled in for a few minutes. The reaction was stirred under a H2 balloon at 23° C. overnight. The solution was filtered through Celite and was concentrated to yield tert-butyl 4-cyano-4-(2-(3-ethoxy-3-oxopropyl)phenyl)piperidine-1-carboxylate. 1H NMR (400 MHz, CDCl3): δ 7.32-7.30 (m, 2H), 7.26-7.24 (m, 2H), 4.28 (bd, 2H), 4.17 (q, 2H), 3.29-3.25 (m, 4H), 2.78-2.74 (m, 2H), 2.34-2.30 (m, 2H), 1.91 (td, 2H), 1.48 (s, 9H), 1.26 (t, 3H). LC/MS RT (5 min method)=2.19 min. Mass observed: 287.22 (M-Boc+H).

Workup

  1. customThe solution was degassed with Ar for 2 min
  2. additionPd/C (10%, 30 mg) was added
  3. customH2 was bubbled in for a few minutes
  4. filtrationThe solution was filtered through Celite
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-ee42cf12123d45a2a17f91f3986d5a19
Source dataset
uspto-grants-2014_10
Patent number
US08859776B2

Reaction notes

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