Triacetoxyperiodinane → Tert-butyl 3-acetyl-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate

HRID 1908010Notes

Reaction equation

[OH:1][CH:2]([CH:4]1[C:13]2([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[O:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:26])[CH3:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:2]([CH:4]1[C:13]2([CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)[O:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:26])(=[O:1])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of tert-butyl 3-(1-hydroxyethyl)-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate (600 mg, 1.66 mmol) and Dess-Martin periodinane (8.3 mL of 0.30 M, 2.5 mmol) was stirred at 25° C. for 5 h. The reaction mixture was diluted with dichloromethane, washed with saturated aqueous NaHCO3 (2×), 5% Na2S2O3 (2×), brine, dried over MgSO4, filtered and concentrated to dryness. Purification by silica gel chromatography provided tert-butyl 3-acetyl-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate (435 mg, 73%). ESI-MS m/z calc. 359.2. found 360.4 (M+1)+; Retention time: 2.84 minutes (4 min run). 1H NMR (400 MHz, CDCl3) δ 7.86 (dd, J=7.8, 1.5 Hz, 1H), 7.60-7.52 (m, 1H), 7.07-7.01 (m, 2H), 4.10-3.79 (m, 2H), 3.76 (s, 1H), 3.29-3.03 (m, 2H), 2.27 (s, 3H), 2.10-1.85 (m, 3H), 1.68-1.58 (m, 1H), 1.47 (s, 9H).

Workup

washwashed with saturated aqueous NaHCO3 (2×), 5% Na2S2O3 (2×), brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to dryness
customPurification by silica gel chromatography

Sources & evidence

ORD record: ord-6e363caf8e00417b8cc819dbe1002a74
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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