Trifluoroacetic acid → HCID 58550931, compound

HRID 2204142Notes

Reaction equation

HRID 2204142 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)=[C:6]([OH:8])[CH:7]=1.O=[C:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]3[CH:13]=[CH:12][CH:11]=[C:10]3[C:15]3([CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[O:8][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 714438HCID 714438, compoundHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 58550931HCID 58550931, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-methyl-2-pyrrol-1-yl-phenol (6.0 g, 33.6 mmol) in dichloromethane (75 mL) was added tert-butyl 4-oxopiperidine-1-carboxylate (6.61 g, 33.6 mmol) then trifluoroacetic acid (3.1 mL, 40.3 mmol) and the mixture was stirred at room temperature for 5.5 hours. The solvent was evaporated and the crude residue was purified by column chromatography utilizing a gradient of 0-100% dichloromethane in hexanes to yield tert-butyl 7′-methylspiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (7.1 g, 59%). 1H NMR (400 MHz, CDCl3) δ 7.22 (d, J=8.1 Hz, 1H), 7.12-7.09 (m, 1H), 6.88 (s, 1H), 6.82 (d, J=8.0 Hz, 1H), 6.29 (t, J=3.2 Hz, 1H), 6.00-5.98 (m, 1H), 5.30 (s, 1H), 3.97 (s, 2H), 3.26 (t, J=12.2 Hz, 2H), 2.32 (s, 3H), 2.09-2.01 (m, 2H), 1.87 (dt, J=13.3, 4.9 Hz, 2H), 1.48 (s, 9H). ESI-MS m/z calc. 354.4, found 355.5 (M+1)+; Retention time 2.28 minutes (3 min run).

Workup

  1. customThe solvent was evaporated
  2. customthe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-6a664d87c17b4eb7bd9eb4249593a040
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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