HCID 123432003, compound → HCID 123565669, compound

HRID 1854571Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:20][CH:21]=[O:22])[C@H:12]([CH3:23])[N:11]1[C:24](=[O:34])[CH2:25][C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:35][Mg]Cl>C1COCC1>[Si:1]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:20][CH:21]([OH:22])[CH3:35])[C@H:12]([CH3:23])[N:11]1[C:24](=[O:34])[CH2:25][C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Dissolve 2-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-(2-(2,6-dichlorophenyl)acetyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl)acetaldehyde (138 mg, 0.27 mmol) in THF (2.7 mL). Cool to 0° C., add MeMgCl (0.097 mL, 0.29 mmol, 3M in Et2O). Stir 30 min at 0° C. Add water and extract with ethyl acetate three times. Combine the ethyl acetate extracts, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by silica gel chromatography, eluting with ethyl acetate: hexanes (gradient, 2-60%) to give the title compound as a white foam (122 mg, 0.23 mmol). MS (m/z): 536.2 (M+1).

Workup

extractionAdd water and extract with ethyl acetate three times
dry with materialdry over sodium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customto give a residue
customPurify the residue by silica gel chromatography
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-cb0f4c72ec55459481b88dfb963ad0c2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962654B2

Reaction notes

Loading…