Piperonyl alcohol → HCID 69763083, compound

HRID 2297982Notes

Reaction equation

HRID 2297982 reaction equation
[CH2:1]1[O:36][C:35]2[CH:34]=[CH:33][C:5]([CH2:6][O:7][C:8](=[O:32])[C@H:9]([NH:18][S:19]([C:22]3[C:27]([CH3:28])=[CH:26][C:25]([O:29][CH3:30])=[CH:24][C:23]=3[CH3:31])(=[O:21])=[O:20])[CH2:10][O:11][CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)=[CH:4][C:3]=2[O:2]1.[CH2:37]1[O:45][C:44]2[CH:43]=[CH:42][C:41]([CH2:46]O)=[CH:40][C:39]=2[O:38]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1>[CH2:1]1[O:36][C:35]2[CH:34]=[CH:33][C:5]([CH2:6][O:7][C:8](=[O:32])[C@H:9]([N:18]([CH2:46][C:41]3[CH:42]=[CH:43][C:44]4[O:45][CH2:37][O:38][C:39]=4[CH:40]=3)[S:19]([C:22]3[C:27]([CH3:28])=[CH:26][C:25]([O:29][CH3:30])=[CH:24][C:23]=3[CH3:31])(=[O:21])=[O:20])[CH2:10][O:11][CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 4

HCID 10322Piperonyl alcoholHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 69763206HCID 69763206, compound

Product 1

HCID 69763083HCID 69763083, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2(R)-(4-methoxy-2,6-dimethylbenzenesulfonyl-amino)-3-(tetrahydropyran-2-yloxy)propionic acid 3,4-methylenedioxybenzyl ester (9.0 g, 16.8 mmol) in benzene (150 mL) at 0° C. was added 3,4-methylenedioxyphenyl methanol (3.8 g, 25.2 mmol), tri-n-butylphosphine (5.1 g, 25.2 mmol), followed by 1,1′-[azodicarbonyl]dipiperidine (6.35 g, 25.2 mmol). The reaction mixture was allowed to warm to room temperature over 4 h. After 16 h, the reaction mixture was diluted with an equal volume of hexanes, cooled to 0° C. for 2 h and filtered. The residue was chromatographed (300 g SiO2, 15% ethyl acetate-hexanes) to afford 2(R)-[(3,4-methylenedioxybenzyl)-(4-methoxy-2,6-dimethylbenzenesulfonyl)amino]-3-(tetrahydropyran-2-yloxy)propionic acid 3,4-methylenedioxybenzyl ester (10.0 g) as a pale orange oil.

Workup

  1. temperaturecooled to 0° C. for 2 h
  2. filtrationfiltered
  3. customThe residue was chromatographed (300 g SiO2, 15% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-cadfc72eb2e04d90b7909bb3dab6db45
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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