Isatin → (R)-1-((tetrahydrofuran-2-yl)methyl)indoline-2,3-dione

HRID 2385013Notes

Reaction equation

[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].Cl[C:13]1[CH:21]=CC=C2[C:14]=1[C:15](=[O:23])[C:16](=O)N2.CC1C=CC(S(OC[C@H]2CCCO2)(=O)=O)=CC=1.BrC(C1C=CC=CC=1)C1C=CC=CC=1>>[O:23]1[CH2:21][CH2:13][CH2:14][C@@H:15]1[CH2:16][N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3]

Participants

Reactant 4

HCID 7054Isatin

HCID 960474-Chloroisatin

HCID 236603Bromodiphenylmethane

HCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 67358326(R)-1-((tetrahydrofuran-2-yl)methyl)indoline-2,3-dione

Procedure

Following the procedure as described in PREPARATION 4A, and making non-critical variations using isatin to replace 4-chloroisatin, and (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate to replace bromodiphenylmethane, 1-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-indole-2,3-dione was obtained (47%) as a thick red oil: 1H NMR (300 MHz, CDCl3) δ7.60-7.54 (m, 2H), 7.14-7.07 (m, 2H), 4.25-4.17 (m, 1H), 3.92-3.82 (m, 2H), 3.78-3.69 (m, 2H), 2.13-2.02 (m, 1H), 1.98-1.85 (m, 2H), 1.74-1.65 (m, 1H); 13C NMR (75 MHz, CDCl3) δ183.5, 158.8, 151.8, 138.5, 125.3, 123.8, 117.7, 111.7, 68.4, 44.7, 29.3, 25.8; MS (ES+) m/z 232.1 (M+1).

Sources & evidence

ORD record: ord-0e5e421ac95244f7a146b85f294bdb62
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263606B2

Reaction notes

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