Trifluoroacetic acid methylene chloride → 2-(4-Bromobenzyl)-8-(4-(SR)-phenylpyrrolidin-3-(RS)-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one
Reaction equation
C(OC([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH2:19][N:20]2[CH2:38][CH2:37][C:23]3([C:27](=[O:28])[N:26]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][CH:31]=4)[CH2:25][CH2:24]3)[CH2:22][CH2:21]2)[CH2:9]1)=O)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[Br:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][N:26]2[CH2:25][CH2:24][C:23]3([CH2:22][CH2:21][N:20]([CH2:19][CH:10]4[CH:11]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=5)[CH2:12][NH:8][CH2:9]4)[CH2:38][CH2:37]3)[C:27]2=[O:28])=[CH:35][CH:34]=1Participants
3
Reactant 2
Product 1
Procedure
To 510 mg (0.87 mmol) of 3-(RS)-[2-(4-bromobenzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-(SR)-phenylpyrroli-dine-1-carboxylic acid tert-butyl ester was added a solution of DCM/TFA 20% (12 mL). The reaction mixture was agitated for one hour at room temperature before quenching with 30 mL of aqueous solution of sodium hydroxide (1N). The solution was then extracted with DCM (2×20 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated in vacuo yielding Compound 3 as a pale yellow solid (420 mg, 99.4%).
Workup
- custombefore quenching with 30 mL of aqueous solution of sodium hydroxide (1N)
- extractionThe solution was then extracted with DCM (2×20 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-bd8d522596704e75acd5a0b8e9877fd9
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07288548B2
Reaction notes
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