tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate → HCID 71270895, compound

HRID 1525888Notes

Reaction equation

HRID 1525888 reaction equation
[Si:1]([O:8][CH2:9][C:10]1([NH2:13])[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:14]1[C:16]2([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:15]1>C(O)C>[Si:1]([O:8][CH2:9][C:10]1([NH:13][CH2:15][C:16]2([OH:14])[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH2:21]2)[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylateHCID 69084009HCID 69084009, compound

Product 1

HCID 71270895HCID 71270895, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(((tert-butyldimethylsilyl)oxy)methyl)cyclopropanamine (10.09 mmol) in absolute ethanol (40 mL) was added tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (9.61 mmol) in one portion. The reaction was heated at reflux for 20 h then cooled and evaporated onto silica. The solid was purified by flash chromatography (30-80% ethyl acetate in hexanes) to afford the title product (719 mg, 16% yield) as a colorless oil. MS(ES)+ m/e 415.5 [M+H]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 20 h
  3. temperaturethen cooled
  4. customevaporated onto silica
  5. customThe solid was purified by flash chromatography (30-80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-cb99307d12aa4266abaadfb77d4ba770
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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