4-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one → tert-butyl 9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-6,9-diazaspiro[4.5]decane-6-carboxylate

HRID 2281290Notes

Reaction equation

HRID 2281290 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[C@@H:12]1[CH2:14][O:13]1.[CH2:15]1[C:19]2([CH2:24][NH:23][CH2:22][CH2:21][N:20]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:18][CH2:17][CH2:16]1>C(O)C>[OH:13][C@H:12]([C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:11])[O:8][CH2:9][C:10]=2[C:2]=1[CH3:1])[CH2:14][N:23]1[CH2:24][C:19]2([CH2:18][CH2:17][CH2:16][CH2:15]2)[N:20]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one2×HCID 68089093Tert-butyl 6,9-diazaspiro[4.5]decane-6-carboxylate

Product 1

HCID 117642078tert-butyl 9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-6,9-diazaspiro[4.5]decane-6-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1 (3H)-one (INTERMEDIATE 2) (38 mg, 0.20 mmol) in 2 mL ethanol was added to tert-butyl 6,9-diazaspiro[4.5]decane-6-carboxylate (42 mg, 0.20 mmol). The reaction mixture was microwaved at 140° C. for 55 minutes. The solvents were removed in vacuo to provide tert-butyl 9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-6,9-diazaspiro[4.5]decane-6-carboxylate which was carried on without further purification.

Workup

  1. customThe reaction mixture was microwaved at 140° C. for 55 minutes
  2. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-0f8a6b7ef0cd406e822125dc7464bea0
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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