Pyrrolidine → HCID 86615343, compound

HRID 1622186Notes

Reaction equation

HRID 1622186 reaction equation
[C:1]1([C@H:11]([NH:13][C@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]3[CH:43]=[CH:42][C:23]([C:24]([C@:26]([C@H:30]([C@@H:32]([C@@H:34]([C:36]([O:38]CC=C)=[O:37])[OH:35])[OH:33])[OH:31])([OH:29])[CH:27]=[O:28])=[O:25])=[CH:22][CH:21]=3)[CH2:15]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.N1CCCC1>O1CCCC1>[C:1]1([C@H:11]([NH:13][C@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]3[CH:43]=[CH:42][C:23]([C:24]([C@:26]([C@H:30]([C@@H:32]([C@@H:34]([C:36]([OH:38])=[O:37])[OH:35])[OH:33])[OH:31])([OH:29])[CH:27]=[O:28])=[O:25])=[CH:22][CH:21]=3)[CH2:15]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 86615344HCID 86615344, compound

Product 1

HCID 86615343HCID 86615343, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 6 ml of tetrahydrofuran was dissolved 615 mg of allyl 2-[4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethyl]aminopiperidin-1-yl]-benzoyl]-D-glucuronate, and the mixture was stirred under ice-cooling and in nitrogen atmosphere. To the mixture were added 91 μl of pyrrolidine, and then, 123 mg of tetrakistriphenylphosphine palladium, and the resulting mixture was stirred for 30 minutes. The residue obtained by concentration under reduced pressure was purified by LC-MS. Ether was added to the obtained solid, the solid was pulverized, collected by filtration, and dried to obtain 220 mg of 2-[4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethyl]aminopiperidin-1-yl]-benzoyl]-D-glucuronic acid (Example 12.030 in the following Table X). (HPLC purity: 67.7%)

Workup

  1. temperaturecooling and in nitrogen atmosphere
  2. customThe residue obtained by concentration under reduced pressure
  3. customwas purified by LC-MS
  4. additionEther was added to the obtained solid
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-8372745fe8134766856454e020c8d191
Source dataset
uspto-grants-2014_07
Patent number
US08778628B2

Reaction notes

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