Benzyl Alcohol → tert-Butyl 4-{[(benzyloxy)carbonyl]amino}-4-methylpiperidine-1-carboxylate

HRID 1943201Notes

Reaction equation

[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:17])(C(O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].C([N:20]([CH2:23]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.[CH2:42]([OH:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH3:17][C:11]1([NH:20][C:23]([O:49][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:32])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-methyl-4-piperidinecarboxylic acid (12.092 g, 49.7 mmol) in toluene (300 ml) was treated with triethylamine (13.85 ml, 99 mmol) and then diphenylphosphoryl azide (21.42 ml, 99 mmol), heated to 90° C. for 2 h (bubbling observed) before treatment with benzyl alcohol (10.34 ml, 99 mmol). The reaction was then heated at 90° C. for a further 18 h, then cooled, treated with saturated aqueous sodium bicarbonate (500 ml), the organic extracts were separated and the aqueous extracted with diethyl ether (200 ml), the combined organic extracts were dried (MgSO4), filtered, evaporated, columned (0-50% ethyl acetate:40-60 petroleum ether, Rf=0.4 in 4:1 ethyl acetate:40-60 petroleum ether) to give product as a clear oil (15.473 g, 89%).

Workup

temperaturecooled
customthe organic extracts were separated
extractionthe aqueous extracted with diethyl ether (200 ml)
dry with materialthe combined organic extracts were dried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-d538c5687cdf465e9275f39dd5e52c8e
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389524B2

Reaction notes

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