Cyclopentanecarbonyl chloride → HCID 57889090, compound

HRID 1016210Notes

Reaction equation

HRID 1016210 reaction equation
[Cl-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@@:9]2([OH:23])[CH2:14][CH2:13][N:12]([C:15](=[O:20])[C@H:16]([NH3+:19])[CH2:17][CH3:18])[CH2:11][C:10]2([CH3:22])[CH3:21])=[CH:5][CH:4]=1.[CH:24]1([C:29](Cl)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C@@:9]2([OH:23])[CH2:14][CH2:13][N:12]([C:15](=[O:20])[C@H:16]([NH:19][C:29]([CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:30])[CH2:17][CH3:18])[CH2:11][C:10]2([CH3:22])[CH3:21])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 78284Cyclopentanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 86614930(R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-1-oxobutan-2-aminium chloride

Product 1

HCID 57889090HCID 57889090, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-1-oxobutan-2-aminium chloride (52.4 mg, 0.14 mmol), cyclopentane carbonylchloride (20 mg, 0.17 mmol), THF (5 mL), and DIPEA (135 mg, 1.1 mmol) were stirred overnight at rt. The reaction was concentrated, and Example 627 was isolated as a white solid using preparative reverse-phase HPLC (30.75 mg, 52.3% yield), M+H=421.31.

Workup

  1. concentrationThe reaction was concentrated
  2. customExample 627 was isolated as a white solid

Sources & evidence

ORD record
ord-a0535fd462f54b5c82be4d2cb5f49baa
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

Loading…