Acetic Acid → HCID 18335092, compound

HRID 390382Notes

Reaction equation

HRID 390382 reaction equation
[N:1]1([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][CH2:7]2)[CH2:3][CH2:2]1.C=O.[C:27](O)(=O)C.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO>[CH3:27][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4]2([CH2:3][CH2:2][N:1]([C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])[CH2:6][CH2:5]2)[CH2:7]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 10914256Benzyl 1,2-dihydrospiro[indole-3,4'-piperidine]-1'-carboxylate

Product 1

HCID 18335092HCID 18335092, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of benzyl spiro[indoline-3,4′-piperidine]-1′-carboxylate (1.15 g, 3.56 mmol), formaldehyde (37% aqueous solution, 1.44 mL, 17.83 mmol) and acetic acid (1.02 mL, 17.83 mmol) in methanol (25 mL) is added sodium cyanoborohydride (0.67 g, 10.68 mmol). The reaction mixture is allowed to warm to room temperature overnight. The pH of the mixture is adjusted to approximately 8 with 10% NaHCO3 solution and extracted with EtOAc (3×50 mL). The combined extracts are washed with water (50 mL) and brine (50 mL), dried, filtered, and evaporated to dryness. The crude material is purified by silica gel chromatography, eluting with hexane:ethyl acetate (85:15) to give the title compound as an off-white solid (0.9 g, 75%). ESI/MS m/z 337.2 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined extracts are washed with water (50 mL) and brine (50 mL)
  3. customdried
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude material is purified by silica gel chromatography
  7. washeluting with hexane:ethyl acetate (85:15)

Sources & evidence

ORD record
ord-987ca30390754174bccf5de80f935aa9
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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