Lithium triethylborohydride → benzyl 5-(hydroxymethyl)-6-iodo-1,3-dihydro-2H-isoindole-2-carboxylate

HRID 604632Notes

Reaction equation

[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:8]2)=[CH:4][C:3]=1[C:21](OC)=[O:22].[Li+].[B-](CC)(CC)CC>C1COCC1>[OH:22][CH2:21][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[I:1])[CH2:8][N:7]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:6]2

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-benzyl 5-methyl 6-iodo-1,3-dihydro-2H-isoindole-2,5-dicarboxylate (104 mg, 0.238 mmol) in THF (5 mL) at −78° C. under N2, was added dropwise 1N Super Hydride in THF (476 uL, 0.476 mmol). The mixture was stirred at −78° C. for 2 h. The reaction mixture was quenched with 1N HCl. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to provide benzyl 5-(hydroxymethyl)-6-iodo-1,3-dihydro-2H-isoindole-2-carboxylate. LCMS calc.=432.0; found=431.9 (M+Na)+. 1H NMR (500 MHz, CDCl3): δ 7.76-7.70 (2 s, 1H); 7.45-7.35 (m, 6H); 5.24 (s, 2H); 4.76-4.67 (m, 4H); 2.18 (br s, 1H).

Workup

customThe reaction mixture was quenched with 1N HCl
extractionThe aqueous layer was extracted with EtOAc (3×)
washThe combined organic layers were washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-3a43b78818df472e8d14d5915adb0231
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910592B2

Reaction notes

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