Acetic Acid → 2-[(3R*,4S*)-1-{[2-Chloro-6-(trifluoromethyl)phenyl]methyl}-3-{[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamoyl}-4-methylpyrrolidin-3-yl]acetic acid

HRID 446021Notes

Reaction equation

HRID 446021 reaction equation
[C:1]1([CH:7]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[C:29]=1[CH2:38][N:39]1[CH2:43][C@@H:42]([CH3:44])[C@@:41]([CH2:54][C:55]([OH:57])=[O:56])([C:45](=[O:53])[NH:46][CH:47]2[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)[CH2:40]1>O1CCCC1.CO.O>[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:37])[F:36])[C:29]=1[CH2:38][N:39]1[CH2:43][C@@H:42]([CH3:44])[C@@:41]([CH2:54][C:55]([OH:57])=[O:56])([C:45](=[O:53])[NH:46][CH:47]2[CH2:48][CH2:49][N:50]([CH2:7][C:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=3)[CH2:51][CH2:52]2)[CH2:40]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 51845401-Cyclohexene-1-carboxaldehydeHCID 712937542-[(3R*,4S*)-1-{[2-Chloro-6-(trifluoromethyl)phenyl]methyl}-4-methyl-3-[(piperidin-4-yl)carbamoyl]pyrrolidin-3-yl]acetic acid

Product 1

HCID 712936432-[(3R*,4S*)-1-{[2-Chloro-6-(trifluoromethyl)phenyl]methyl}-3-{[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamoyl}-4-methylpyrrolidin-3-yl]acetic acidYield 70.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cyclohex-1-ene-1-carbaldehyde (25.9 μl, 0.227 mmol), acetic acid (30 μl) and sodium triacetoxyborohydride (68.8 mg, 0.325 mmol) were added to a solution of 2-[(3R*,4S*)-1-{[2-chloro-6-(trifluoromethyl)phenyl]methyl}-4-methyl-3-[(piperidin-4-yl)carbamoyl]pyrrolidin-3-yl]acetic acid obtained by the method of Example 5d (15 mg, 0.0325 mmol) in tetrahydrofuran (dehydrated) (2 mL), followed by stirring overnight. Water and methanol were added to the reaction liquid, which was concentrated under reduced pressure, and the residue was purified by ODS column chromatography (elution solvent: water/methanol) to give the title compound (12.8 mg, yield: 70.8%).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customthe residue was purified by ODS column chromatography (elution solvent: water/methanol)

Sources & evidence

ORD record
ord-7d9abee4e15a44288a45985dce9d93ad
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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