Water → (1R,2R)-1-(3-chlorophenyl)-2-{2-[(phenylmethyl)oxy]ethyl}cyclopropanecarbonitrile

HRID 2099295Notes

Reaction equation

[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CC1C=CC(S(O[C@H:22]([CH2:34][CH2:35][O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:23][CH:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=2)[C:25]#[N:26])(=O)=O)=CC=1.O>CN(C=O)C>[Cl:33][C:29]1[CH:28]=[C:27]([C@@:24]2([C:25]#[N:26])[CH2:23][C@@H:22]2[CH2:34][CH2:35][O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: -40 °C

Procedure

3.2 mL 1M LHMDS in hexanes (3.2 mmol) was added to 15 mL of DMF and cooled to −40° C. To this was added a solution of (1S)-3-(3-chlorophenyl)-3-cyano-1-(2-[(phenylmethyl)oxy]ethyl}propyl 4-methylbenzenesulfonate (1.00 g, 2.12 mmol) in 5 mL of DMF over 10 minutes and stirred for 40 minutes After warming to room temperature the reaction was stirred until no starting material remained by TLC. The reaction mixture was poured into 100 mL water, extracted with 50 mL EtOAc, the organic phase isolated, washed with brine and dried over MgSO4. The resulting residue was purified by silica gel chromatography with 25% EtOAc in hexanes to give the title compound (436 mg, 65% yield). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.4 (dd, J=7.5, 5.6 Hz, 1H) 1.5 (m, 1H) 1.7 (m, 1H) 2.0 (m, 2H) 3.6 (m, 2H) 4.5 (d, J=2.2 Hz, 2H) 7.1 (m, 1H) 7.2 (m, 3H) 7.3 (m, 5H).

Workup

temperatureAfter warming to room temperature the reaction
stirringwas stirred until no starting material
extractionextracted with 50 mL EtOAc
customthe organic phase isolated
washwashed with brine
dry with materialdried over MgSO4
customThe resulting residue was purified by silica gel chromatography with 25% EtOAc in hexanes

Sources & evidence

ORD record: ord-339958cf78bf4f4e8e48fd7f711acd47
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569579B2

Reaction notes

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