Styrene Oxide → 2-(4-Cyclopropyl-phenyl)-8-(2-hydroxy-2-phenyl-ethyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 1942220Notes

Reaction equation

HRID 1942220 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:21]1([CH:27]2[CH2:29][O:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN(CC)CC>C(Cl)Cl>[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]([CH2:29][CH:27]([OH:28])[C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH2:16][CH2:15]4)[C:11]3=[O:20])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7276Styrene OxideHCID 8471TriethylamineHCID 582872772-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

Product 1

HCID 532325362-(4-Cyclopropyl-phenyl)-8-(2-hydroxy-2-phenyl-ethyl)-2,8-diaza-spiro[4.5]decan-1-oneYield 14.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 34.6 mg (0.128 mmol) 2-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one, 23 mg (0.192 mmol) 2-phenyl-oxirane and 38 mg (0.384 mmol) NEt3 in 2 mL DCM were stirred at 50° C. for 2 h and concentrated. 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 (14%) of the title compound. MS m/e: 391.4 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customsubjected to purification by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and NEt3
  5. additionThe product containing fractions
  6. customwere evaporated

Sources & evidence

ORD record
ord-88ed3773d0dd43b285c5cb7db610f96f
Source dataset
uspto-grants-2013_03
Patent number
US08389539B2

Reaction notes

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