Hexane → 1-Benzyloxycarbonyl-4-hydroxy-4-(2-methylthiophenyl)piperidine

HRID 2256046Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:9].CCCCCC.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>O1CCCC1.O>[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[S:8][CH3:9])[CH2:33][CH2:32]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 6 °C

Procedure

A solution of 2-bromothioanisole (1.05 g) in 20 mL of anhydrous tetrahydrofuran was cooled to -78° C. and treated with 2 mL of 2.5M hexane solution of n-butyl lithium. After the addition was complete the reaction mixture was stirred for 30 minutes and then treated with a solution of N-benzyloxycarbonyl-4-oxopiperidine (1.17 g) in 1 mL of tetrahydrofuran. After stirring at -78° C. for 30 minutes the reaction mixture was allowed to warm to 6° C. and treated with 10 mL of water. Upon extracting with ethyl acetate, drying and evaporation, the organic layer afforded the crude product. This material was purified by chromatography; elution with 6:4 hexane:ethyl acetate afforded the named material (0.27 g); MS: 358; NMR: 1.9-2.1 (b, 4), 2.5 (s, 3), 3.4 (b, 2), 4.1b (b, 2), 5.1 (s, 2), 7.1-7.5 (m, 9).

Workup

additionAfter the addition
stirringAfter stirring at -78° C. for 30 minutes the reaction mixture
extractionUpon extracting with ethyl acetate
customdrying
customevaporation
customthe organic layer afforded the crude product
customThis material was purified by chromatography
washelution with 6:4 hexane

Sources & evidence

ORD record: ord-ce4706611bec49a7bc2cf8092cd5ebf0
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05654299

Reaction notes

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