Acetic Acid → 2-(4-Cyclopropyl-phenyl)-8-(3-phenyl-propyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 1942216Notes

Reaction equation

HRID 1942216 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([N:10]3[CH2:14][CH2:13][C:12]4([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[C:11]3=[O:20])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C(O)(=O)C.[Na].[C:26]1([CH2:32][CH2:33][CH:34]=O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.O>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([N:10]3[CH2:14][CH2:13][C:12]4([CH2:19][CH2:18][N:17]([CH2:34][CH2:33][CH2:32][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH2:16][CH2:15]4)[C:11]3=[O:20])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7707BenzenepropanalHCID 5360545SodiumHCID 582872772-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

Product 1

HCID 532338662-(4-Cyclopropyl-phenyl)-8-(3-phenyl-propyl)-2,8-diaza-spiro[4.5]decan-1-oneYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 20 mg (0.074 mmol) 2-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one, 42 uL acetic acid, 44 mg (0.148 mmol) sodium triacetyoxyborohydride and excess 3-phenyl-propionaldehyde in 2 mL THF was stirred for at room temperature over night. Water was added, the mixture was extracted with ethyl acetate and the combined organic layers were evaporated to dryness. The residue was taken up in methanol and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. The product containing fractions were evaporated to yield 7.1 mg (25%) of the title compound. MS m/e: 389.4 [M+H]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customthe combined organic layers were evaporated to dryness
  3. customsubjected to purification by preparative HPLC on reversed phase
  4. washeluting with a gradient
  5. customformed from acetonitrile, water and NEt3
  6. additionThe product containing fractions
  7. customwere evaporated

Sources & evidence

ORD record
ord-10015ebfb1cf410a8d8fbb3494b03f24
Source dataset
uspto-grants-2013_03
Patent number
US08389539B2

Reaction notes

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