Trifluoroacetic acid → HCID 59352434, compound

HRID 422847Notes

Reaction equation

HRID 422847 reaction equation
[O:1]=[C:2]1[C:10]2([CH2:14][O:13][C:12]3[CH:15]=[C:16]4[C:20](=[CH:21][C:11]2=3)[CH2:19][CH2:18][O:17]4)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:22][C@@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1C(OC(C)(C)C)=O.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[NH:24]1[CH2:25][CH2:26][CH2:27][C@H:23]1[CH2:22][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]2([CH2:14][O:13][C:12]3[CH:15]=[C:16]4[C:20](=[CH:21][C:11]2=3)[CH2:19][CH2:18][O:17]4)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 66672802HCID 66672802, compound

Product 1

HCID 59352434HCID 59352434, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (2S)-2-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]pyrrolidine-1-carboxylate (0.74 g, 1.60 mmol) and trifluoroacetic acid (1.6 mL) in dichloromethane (8 mL) was stirred at ambient temperature for 80 h. The reaction was made basic with 1 M sodium hydroxide (30 mL) and was extracted with dichloromethane (3×25 mL). The combined organic solution was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 1′-[(2S)-pyrrolidin-2-ylmethyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.51 g, 89%) as a pale yellow solid: mp 83-86° C. (hexanes); 1H NMR (300 MHz, CDCl3) (diastereomers) δ 7.29 (dd, J=7.8, 7.5 Hz, 1H), 7.16 (d, J=7.5 Hz, 1H), 7.07-6.99 (m, 2H), 6.52, 6.46 (s, 1H), 6.40 (s, 1H), 4.95, 4.91 (d, J=9.0 Hz, 1H), 4.66 (d, J=9.0 Hz, 1H), 4.53 (t, J=8.7 Hz, 2H), 3.91-3.71 (m, 2H), 3.69-3.60 (m, 1H), 3.14-2.90 (m, 5H), 1.98-1.70 (m, 3H), 1.66-1.51 (m, 1H); MS (ES+) m/z 363.1 (M+1).

Workup

  1. extractionwas extracted with dichloromethane (3×25 mL)
  2. dry with materialThe combined organic solution was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20c93c5088e64d7d923160d385f2b81a
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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