Benzyl Alcohol → (8-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamic acid benzyl ester

HRID 2235218Notes

Reaction equation

C[C:2]1([C:12](O)=O)[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[CH2:39]([OH:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1C=CC=CC=1>[CH2:39]([O:46][C:20](=[O:29])[NH:17][C:2]1([CH3:12])[CH2:3][CH2:4][C:5]2([O:6][CH2:7][CH2:8][O:9]2)[CH2:10][CH2:11]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve 8-methyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid (Chem. Pharm. Bull., 1984, 32(6), 2267-2278) (10.9 g, 54.4 mmol) in benzene (500 mL). Add triethylamine (6.61 g, 65.32 mmol), diphenylphosphoryl azide (16.48 g, 59.88 mmol), and benzyl alcohol (8.83 g, 81.66 mmol) under nitrogen. Stir and heat the reaction mixture to 80° C. Continue to heat the reaction at 80° C. for 8 hours, then cool to room temperature. Add water (500 mL), and extract the aqueous layer with ethyl acetate (3×500 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 5-25% of EtOAc/Hexane) to give 13.45 g (81%) of (8-Methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamic acid benzyl ester as a colorless oil.

Workup

temperatureto heat
customthe reaction at 80° C. for 8 hours
temperaturecool to room temperature
extractionAdd water (500 mL), and extract the aqueous layer with ethyl acetate (3×500 mL)
dry with materialCombine the organic layers and dry with Na2SO4
filtrationfilter
concentrationconcentrate
custompurify by flash column chromatography (silica gel, 5-25% of EtOAc/Hexane)

Sources & evidence

ORD record: ord-7f671fc2dd394b4c8efff51be76b4b56
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713979B2

Reaction notes

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