Water → HCID 22622324, compound

HRID 2256055Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([Li])CCC.[CH2:21]([O:28][C:29]([N:31]1[CH2:36][CH2:35][C:34](=[O:37])[CH2:33][CH2:32]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH2:21]([O:28][C:29]([N:31]1[CH2:36][CH2:35][C:34]([OH:37])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:33][CH2:32]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of benzyl 2-bromophenyl ether (3.5 g) in 50 mL of anhydrous tetrahydrofuran was cooled to -78° C. and treated with 5.3 mL of 2.5M n-butyl lithium solution in hexane followed by a solution of 1-benzyloxycarbonyl-4-oxopiperidine (3.1 g) in 3 mL of anhydrous tetrahydrofuran. After stirring at -78° C. for 1 hour the reaction mixture was warmed to 0° C., stirred for 2 hours and then allowed to warm to room temperature. Addition of water, extraction with ethyl acetate, drying the organic layer over magnesium sulfate and evaporation afforded the crude product. This material was purified by chromatography: elution with hexane:isopropanol (9:1) afforded the named compound (2.86 g) as a solid; MS: 418; NMR: 2.0 (br, 4), 3.3-3.4 (br, 2), 3.9-4.1 (s, 3), 5.1 (two s, 4), 6.9-7.0 (m, 2), 7.2-7.3 (m, 2), 7.3-7.4 (m, 10).

Workup

temperaturewas warmed to 0° C.
stirringstirred for 2 hours
temperatureto warm to room temperature
customdrying the organic layer
customover magnesium sulfate and evaporation
customafforded the crude product
customThis material was purified by chromatography
washelution with hexane:isopropanol (9:1)

Sources & evidence

ORD record: ord-7a8dec41940d42e09f299871416abe94
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654299

Reaction notes

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