(Diethylamino)sulfur trifluoride → HCID 59013461, compound

HRID 1716972Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:18](=[CH:19][C:20]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[CH:24][CH:23]=1)[C@:7]1([C@H:12]([OH:13])[C@@H:11]([OH:14])[C@H:10]([OH:15])[C@@H:9]([CH2:16]O)[O:8]1)[CH2:6][CH2:5]2.CCN(S(F)(F)[F:36])CC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:18](=[CH:19][C:20]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[CH:24][CH:23]=1)[C@:7]1([C@H:12]([OH:13])[C@@H:11]([OH:14])[C@H:10]([OH:15])[C@@H:9]([CH2:16][F:36])[O:8]1)[CH2:6][CH2:5]2

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (1S,3′R,4′S,5′S,6′R)-5-chloro-6-(4-ethylbenzyl)-6′-(hydroxymethyl)-2,3,3′,4′,5′,6′-hexahydrospiro[indene-1,2′-pyran]-3′,4′,5′-triol (10 mg, 0.024 mmol) in CH2Cl2 (1 mL), was added DAST (9 μL, 0.072 mmol) at −78° C. The mixture was stirred for 30 min at −78° C., then allowed to warm to room temperature and stirred for another 3 h. The reaction was quenched by aqueous saturated NaHCO3. The organic layer was separated, dried with Na2SO4 and concentrated in vacuo. The resulting residue was purified by preparative HPLC to give 4 mg (40%) of title compound as a colorless solid. 1H NMR (CD3OD, 300 MHz): δ 7.24 (s, 1H), 7.19 (s, 1H), 7.08 (m, 4H), 4.63 (d, J=3.3 Hz, 1H), 4.47 (d, J=3 Hz, 1H), 4.04 (m, 2H), 3.59-3.38 (m, 4H), 2.93 (t, J=7.2 Hz, 2H), 2.58 (q, J=7.8 Hz, 2H), 2.54 (dt, J=13.5, 7.8 Hz, 1H), 2.08 (dt, J=13.5, 7.8 Hz, 1H), 1.19 (t, J=7.8 Hz, 3H).

Workup

temperatureto warm to room temperature
stirringstirred for another 3 h
customThe reaction was quenched by aqueous saturated NaHCO3
customThe organic layer was separated
dry with materialdried with Na2SO4
concentrationconcentrated in vacuo
customThe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-234c394584e747f88991f4eb54a4391b
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803778B2

Reaction notes

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