Cyclopentanone → HCID 10123192, compound

HRID 1278607Notes

Reaction equation

HRID 1278607 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:46])[CH2:16][C:17]3[NH:18][C:19]([CH2:39][CH2:40][C:41]4[S:42][CH:43]=[CH:44][N:45]=4)=[C:20]([C:35]([O:37][CH3:38])=[O:36])[CH:21]([C:27]4[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:34])[C:22]=3[C:23]([O:25][CH3:26])=[O:24])[CH2:11][CH2:10]2)[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:47]1(=O)[CH2:51][CH2:50][CH2:49][CH2:48]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl.CC(O)=O>[CH:47]1([NH:1][CH2:2][C:3]2([CH2:8][N:9]3[CH2:10][CH2:11][N:12]([C:15](=[O:46])[CH2:16][C:17]4[NH:18][C:19]([CH2:39][CH2:40][C:41]5[S:42][CH:43]=[CH:44][N:45]=5)=[C:20]([C:35]([O:37][CH3:38])=[O:36])[CH:21]([C:27]5[C:28]([Cl:34])=[CH:29][CH:30]=[CH:31][C:32]=5[Cl:33])[C:22]=4[C:23]([O:25][CH3:26])=[O:24])[CH2:13][CH2:14]3)[CH2:4][CH2:5][CH2:6][CH2:7]2)[CH2:51][CH2:50][CH2:49][CH2:48]1

Participants

6

Reactant 3

HCID 8452CyclopentanoneHCID 5049666Sodium triacetoxyborohydrideHCID 10146646HCID 10146646, compound

Product 1

HCID 10123192HCID 10123192, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of dimethyl 2-[2-[4-[[1-(aminomethyl)cyclopentyl]methyl]-1-piperazinyl]-2-oxoethyl]-4-(2,6-dichlorophenyl)-6-[2-(1,3-thiazol-2-yl)ethyl]-1,4-dihydro-3,5-pyridinedicarboxylate (205 mg/0.298 mmol) and cyclopentanone (0.032 ml/0.36 mmol) in dichloromethane (2 ml) was added AcOH (1 drop) and the resulting mixture was stirred for 5 minutes. NaBH(OAc)3 (80 mg/0.36 mmol) was added to the mixture and the resulting mixture was stirred for 5 hours. The mixture was diluted with dichloromethane (50 ml) and the resulting solution was washed with water (10 ml) and brine (10 ml) successively. The solution was dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography (NH2 gel/dichloromethane:methanol=100:0-100:2) to give a yellow film (220 mg/98%).

Workup

  1. stirringthe resulting mixture was stirred for 5 hours
  2. washthe resulting solution was washed with water (10 ml) and brine (10 ml) successively
  3. dry with materialThe solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (NH2 gel/dichloromethane:methanol=100:0-100:2)
  7. customto give a yellow film (220 mg/98%)

Sources & evidence

ORD record
ord-516d30a77369415197d78f689d3ee1fe
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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