Piperidine → [1-(Acetylaminomethyl)-2,3-dioxo-3-piperidin-1-yl-propyl]carbamic acid benzyl ester

HRID 1861829Notes

Reaction equation

HRID 1861829 reaction equation
[CH2:1]([O:8][C:9](=[O:41])[NH:10][CH:11]([CH2:36][NH:37][C:38](=[O:40])[CH3:39])[C:12](=[O:35])[C:13](C#N)=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:42]=[O+][O-].[NH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:41])[NH:10][CH:11]([CH2:36][NH:37][C:38](=[O:40])[CH3:39])[C:12](=[O:35])[C:13](=[O:42])[N:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 24823OzoneHCID 86758881[1-(Acetylaminomethyl)-3-cyano-2-oxo-3-(triphenyl-lambda5-phosphanylidene) propyl]carbamic acid benzyl ester

Product 1

HCID 69905735[1-(Acetylaminomethyl)-2,3-dioxo-3-piperidin-1-yl-propyl]carbamic acid benzyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [1-(acetylaminomethyl)-3-cyano-2-oxo-3-(triphenyl-λ5-phosphanylidene) propyl]carbamic acid benzyl ester (prepared as described in Example 10) (572 mg, 1.01 mmol, 1 equiv) in CH2Cl2 (11 mL) at −78° C. was treated with ozone gas for 2 h. The chilled solution was then purged with Ar for 10 min until the color had changed from green to yellow. Piperidine (0.110 mL, 1.12 mmol, 1.1 equiv) was added dropwise over 1 min, and stirring continued at −78° C. for 15 min. The volatiles were removed under reduced pressure, and the residue purified by flash column chromatography (5% CH3OH in CH2Cl2) to give [1-(acetylaminomethyl)-2,3-dioxo-3-piperidin-1-yl-propyl]carbamic acid benzyl ester (120.7 mg, 32% yield) as a colorless foam. Rf=0.30 (EtOAc). IR (cm−1) 3304, 1720, 1639, 1537. 1H NMR (CDCl3) δ1.59 (br s, 7H), 1.97 (s, 3H), 3.22-3.91 (m, 7H), 4.54-4.58 (m, 1H), 5.09 (s, 2H), 6.28 (br s, 1H), 6.67 (br s, 1H), 7.34 (s, 5H).

Workup

  1. customThe chilled solution was then purged with Ar for 10 min until the color
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue purified by flash column chromatography (5% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-daedc3e3fe4248cab209a9cd034c9075
Source dataset
uspto-grants-2003_03
Patent number
US06534530B1

Reaction notes

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