Trifluoroacetic acid → HCID 58551532, compound

HRID 1908055Notes

Reaction equation

HRID 1908055 reaction equation
[NH2:1][N:2]([CH:10]([CH3:12])[CH3:11])C(=O)OC(C)(C)C.O/[CH:14]=[C:15]1\[C:16](=O)[C:17]2[C:22]([O:23][C:24]3\1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[CH2:26][CH2:25]3)=[CH:21][CH:20]=[CH:19][CH:18]=2.C(O)(C(F)(F)F)=O>ClCCl>[CH:10]([N:2]1[C:16]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[O:23][C:24]3([CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])[CH2:26][CH2:25]3)[C:15]=2[CH:14]=[N:1]1)([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10583380175233-53-1HCID 58551170HCID 58551170, compound

Product 1

HCID 58551532HCID 58551532, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl N-amino-N-isopropyl-carbamate (530.4 mg, 3.0 mmol), (Z)-benzyl 3-(hydroxymethylene)-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate (1.10 g, 2.9 mmol) and TFA (223.4 μL, 2.9 mmol) in dichloromethane (10 mL) was stirred 2 h. The reaction was concentrated to ⅓ volume, then TFA (˜1.5 mL) was added. The mixture was stirred for 30 min, then concentrated, neutralized with excess Et3N, re-concentrated, and purified by column chromatography (0-60% EtOAc/hexanes) to give benzyl 1-isopropyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-carboxylate (1.1 g, 91%) as a pale yellow oil. ESI-MS m/z calc. 417.2. found 418.3 (M+1)+; Retention time: 2.07 minutes (3 min run).

Workup

  1. concentrationThe reaction was concentrated
  2. additionTFA (˜1.5 mL) was added
  3. stirringThe mixture was stirred for 30 min
  4. concentrationconcentrated
  5. concentrationre-concentrated
  6. custompurified by column chromatography (0-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d889d952a4b8484d9240857e8d2d656c
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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