Trifluoroacetic acid → Trifluoroacetic acid

HRID 2267113Notes

Reaction equation

HRID 2267113 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:20][CH2:19][C:18]2([C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([C:29]([OH:31])=[O:30])=[CH:21]2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[NH:15]1[CH2:20][CH2:19][C:18]2([C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([C:29]([O-:31])=[O:30])=[CH:21]2)[CH2:17][CH2:16]1.[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 497602001'-(tert-Butoxycarbonyl)spiro[indene-1,4'-piperidine]-3-carboxylic acid

Product 2

HCID 6422Trifluoroacetic acidHCID 86618205Spiro[indene-1,4'piperidine]-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a stirred solution of 1′-(tert-butyoxycarbonyl)spiro[indene-1,4′-piperidine]-3-carboxylic acid (C4) (0.25 g, 0.76 mmol) in dichloromethane (5 mL) and the solution was stirred at room temperature for 1 h. The solvent was removed under reduced pressure and dried under high vacuum for 18 h to provide spiro[indene-1,4′piperidine]-3-carboxylate (D1) as an oil (0.26 g, quantitative, TFA salt). LC/MS (10-90% over 3 min with 0.9% FA) m/z 230.3 (M+1), Rt 1.3 minutes. 1HNMR (500 MHz, DMSO-d6): 12.91 (brs, 1H), 7.95 (s, 1H), 7.88 (d, 1H), 7.35 (m, 3H), 3.31-3.43 (m, 4H), 2.27 (m, 2H), 1.42 (m,2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customdried under high vacuum for 18 h

Sources & evidence

ORD record
ord-c77dfbee048f4ad6a731a3d358d6a404
Source dataset
uspto-grants-2010_12
Patent number
US07858790B2

Reaction notes

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