Formic Acid → HCID 57949399, compound

HRID 2427529Notes

Reaction equation

HRID 2427529 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](C=O)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.C(O)=O.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([CH2:42][NH2:43])[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].C([BH3-])#N.[Na+]>CO.O>[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([CH2:42][NH:43][C:4]2[CH:5]=[C:6]3[C:10](=[C:2]([Cl:1])[CH:3]=2)[C:9](=[O:11])[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:21])([F:23])[F:22])=[CH:15][CH:14]=2)[CH2:7]3)[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 5003444Sodium cyanoborohydrideHCID 57949660HCID 57949660, compound

Product 1

HCID 57949399HCID 57949399, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 7-chloro-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbaldehyde (60 mg, 0.162 mmol) in methanol (1.6 mL) was added formic acid (0.02 ml), 4-Aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (35 mg, 0.162 mmol), and Sodium cyanoborohydride (0.2 mL, 1M in THF) respectively. The mixture stirred at room temperature for 1 hour and was then diluted with water and extracted with ethyl acetate. The organic were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography (56-60% ethyl acetate in hexanes) provided the title compound (47 mg, 52%). 1H NMR (300 MHz, CDCl3): δ (7.35 (d, 4H), 7.18 (d, 2H), 4.77 (s, 2H), 4.25 (s, 2H), 4.13 (br s, 1H), 3.86 (s, 2H), 2.65 (t, 4H), 2.54 (d, 2H), 1.70 (t, 4H), 1.45 (s, 9H)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-505f9a6e540b485f86525b01a8b19688
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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