Acetone → HCID 118383701, compound

HRID 2202701Notes

Reaction equation

[CH3:1][C:2]1([CH3:11])[N:6]2[C:7](=[O:10])[CH2:8][CH2:9][C@@H:5]2[CH2:4][O:3]1.C([N-]C(C)C)(C)C.[Li+].C1COCC1.CCCCCCC.C(C1C=CC=CC=1)C.[CH3:40][C:41]([CH3:43])=[O:42]>C1COCC1>[OH:42][C:41]([CH:8]1[C:7](=[O:10])[N:6]2[C:2]([CH3:11])([CH3:1])[O:3][CH2:4][C@H:5]2[CH2:9]1)([CH3:43])[CH3:40]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (R)-3,3-dimethyltetrahydropyrrolo[1,2-c]oxazol-5(3H)-one (6.68 g, 43.0 mmol) in THF (100 mL) cooled to −78° C., was added lithium diisopropylamide, 2.0 M solution in THF/heptane/ethylbenzene (43.0 mL, 86 mmol) and stirred at −78° C. for 1 h. The resulting mixture was treated with acetone, 99.8%, extra dry, acroseal (6.32 mL, 86 mmol) at −78° C. and then allowed to warm up to room temperature for 16 h. The reaction was quenched with sat. NH4Cl and extracted with EtOAc (2×200 mL). The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated to provide (7aR)-6-(2-hydroxypropan-2-yl)-3,3-dimethyltetrahydropyrrolo[1,2-c]oxazol-5(3H)-one (6.088 g, 28.5 mmol, 66.3% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 4.50 (s, 1H), 4.07-4.18 (m, 1H), 3.98 (dd, J=8.0, 5.7 Hz, 1H), 3.32-3.35 (m, 1H), 2.50-2.56 (m, 1H), 2.22 (ddd, J=13.4, 7.2, 2.0 Hz, 1H), 1.83 (ddd, J=13.3, 10.4, 7.6 Hz, 1H), 1.54 (s, 3H), 1.32 (s, 3H), 1.21 (s, 3H), 1.14 (s, 3H). m/z (ESI, +ve) 214 (M+H).

Workup

temperatureto warm up to room temperature for 16 h
customThe reaction was quenched with sat. NH4Cl
extractionextracted with EtOAc (2×200 mL)
washThe combined extracts were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-59123183a36d4c63b0077bd82821ce32
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365522B2

Reaction notes

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