Ethyl 2-(diphenylmethyleneamino)acetate → (3R)-ethyl 2-(diphenylmethyleneamino)-3-ethyl-5-methylnon-8-enoate

HRID 523189Notes

Reaction equation

CC1C=CC(S(O[C@H:12]([CH2:15][CH:16]([CH3:21])[CH2:17][CH2:18][CH:19]=[CH2:20])[CH2:13][CH3:14])(=O)=O)=CC=1.[CH2:22]([O:24][C:25](=[O:41])[CH2:26][N:27]=[C:28]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:23].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1(C)C=CC=CC=1>[C:29]1([C:28](=[N:27][CH:26]([C@H:12]([CH2:13][CH3:14])[CH2:15][CH:16]([CH3:21])[CH2:17][CH2:18][CH:19]=[CH2:20])[C:25]([O:24][CH2:22][CH3:23])=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of (S)-5-methylnon-8-en-3-yl 4-methylbenzenesulfonate (15 g, 48 mmole) and N-(diphenylmethylene)glycinate ethyl ester (15.5 g, 58.0 mmole) in toluene (150 mL) at 0° C. was added lithium bis(trimethylsilyl)amide (“LiHMDS”, 72.5 mL, 72.5 mmole, 1 M solution in THF). The reaction mass was allowed to come to room temperature, and then was heated at 110° C. for 2 h. The reaction mass was cooled to room temperature, quenched with water and extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4; filtered; then concentrated under reduced pressure to get crude compound (7.0 g, 35.7%). The crude compound was taken to the next step without further purification. MS: MS m/z 406.4 (M++1).

Workup

customto come to room temperature
temperatureThe reaction mass was cooled to room temperature
customquenched with water
extractionextracted with ethyl acetate (100 mL×3)
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
filtrationfiltered
concentrationthen concentrated under reduced pressure

Sources & evidence

ORD record: ord-45414f6d46454177a9d98dc4cd8ad690
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334279B2

Reaction notes

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