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2-(Trifluoromethyl)benzylic alcohol → 2-(Trifluoromethyl)benzyl 7-bromo-3-oxo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

HRID 390193
Notes
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Reaction equation

HRID 390193 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][OH:6].[C:13](C1NC=CN=1)(C1NC=CN=1)=[O:14].[Br:25][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:39]=1[C:33]1([CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)[CH2:32][C:31]2=[O:40]>C(Cl)Cl>[Br:25][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:39]=1[C:33]1([CH2:34][CH2:35][N:36]([C:13]([O:6][CH2:5][C:4]3[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=3[C:2]([F:11])([F:12])[F:1])=[O:14])[CH2:37][CH2:38]1)[CH2:32][C:31]2=[O:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 676662-(Trifluoromethyl)benzylic alcoholHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 582956717-bromospiro[indene-1,4'-piperidin]-3(2H)-one

Product 1

HCID 442270792-(Trifluoromethyl)benzyl 7-bromo-3-oxo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
3×

Procedure

To o-(trifluoromethyl)benzyl alcohol (35 mg, 0.20 mmol) in CH2Cl2 (4 mL) was added was a solution of carbonyl diimidazole (29 mg, 0.18 mmol) in CH2Cl2 (4 mL). The mixture was stirred at rt for 2 h. A 1-mL aliquot of the resulting solution (0.05 mmol) was added to a solution 7-bromospiro[indene-1,4′-piperidin]-3(2H)-one (14.5 mg, 0.05 mmol) in CH2Cl2 (1 mL). The mixture was stirred at rt for 16 h, concentrated, redissolved in MeCN (1 mL) and heated at 60° C. for 2 h. Prep HPLC afforded the title compound. LC-MS Method 1 tR=2.06, min, m/z=484, 482.

Workup

  1. stirringThe mixture was stirred at rt for 16 h
  2. concentrationconcentrated
  3. dissolutionredissolved in MeCN (1 mL)
  4. temperatureheated at 60° C. for 2 h

Sources & evidence

ORD record
ord-67ab8ad46ead4b3d99d43255073f14ae
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08383629B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes