Trifluoroacetic acid → 2-(4-Methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 1182169Notes

Reaction equation

HRID 1182169 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:10]([CH2:19][N:20]2[CH2:39][CH2:38][C:23]3([C:27](=[O:28])[N:26]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)[CH2:25][CH2:24]3)[CH2:22][CH2:21]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[CH3:37][O:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][N:26]2[CH2:25][CH2:24][C:23]3([CH2:38][CH2:39][N:20]([CH2:19][C@@H:10]4[C@@H:11]([C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=5)[CH2:12][NH:8][CH2:9]4)[CH2:21][CH2:22]3)[C:27]2=[O:28])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 11284019(3S,4S)-3-[2-(4-Methoxy-benzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 114646642-(4-Methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-oneYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5.81 g (10.9 mmol) of (3S,4S)-3-[2-(4-methoxy-benzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester in dichloromethane (100 mL) was added trifluoroacetic acid (30 mL) and the solution was stirred for 1 h at room temperature. The reaction mixture was neutralized with 1N NaOH (40 mL) and extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated to give Compound 111 as a white foam (4.42 g, 94%).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-af80b01275f04a63a494a4964aa43d29
Source dataset
uspto-grants-2007_10
Patent number
US07288548B2

Reaction notes

Loading…