4-Morpholinecarbonyl chloride → 2-(4-Methoxy-benzyl)-8-[(3S,4S)-1-(morpholine-4-carbonyl)-4-phenyl-pyrrolidin-3-ylmethyl]-2,8-diaza-spiro[4.5]decan-1-one Hydrochloride

HRID 1182171Notes

Reaction equation

HRID 1182171 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]4[C@@H:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:22][NH:21][CH2:20]4)[CH2:14][CH2:13]3)[C:9]2=[O:30])=[CH:5][CH:4]=1.[N:33]1([C:39]([Cl:41])=[O:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[ClH:41].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]4[C@@H:23]([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH2:22][N:21]([C:39]([N:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)=[O:40])[CH2:20]4)[CH2:14][CH2:13]3)[C:9]2=[O:30])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 848104-Morpholinecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 114646642-(4-Methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one

Product 1

HCID 673689292-(4-Methoxy-benzyl)-8-[(3S,4S)-1-(morpholine-4-carbonyl)-4-phenyl-pyrrolidin-3-ylmethyl]-2,8-diaza-spiro[4.5]decan-1-one HydrochlorideYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one (60 μmol) in anhydrous DCM (1 mL) was added 4-morpholinecarbonyl chloride (21 μL, 180 μmol). The reaction mixture was stirred overnight at room temperature. Saturated sodium bicarbonate aqueous solution was added to the reaction mixture and the aqueous layer washed with DCM (3×2 mL). The organic layer was then concentrated in vacuo and purified by semi-preparative HPLC (Method D) and lyophilized to give Compound 157 as a colorless solid (6.2 mg, 19%).

Workup

  1. washthe aqueous layer washed with DCM (3×2 mL)
  2. concentrationThe organic layer was then concentrated in vacuo
  3. custompurified by semi-preparative HPLC (Method D)

Sources & evidence

ORD record
ord-379697b093c24876be6871dbfc5ac4d5
Source dataset
uspto-grants-2007_10
Patent number
US07288548B2

Reaction notes

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