Diisobutylaluminum hydride → HCID 57775669, compound

HRID 1160181Notes

Reaction equation

HRID 1160181 reaction equation
[CH2:1]([C:8]1([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:12][CH2:11][O:10][C:9]1=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[CH2:1]([C:8]1([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:12][CH2:11][O:10][CH:9]1[OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86632340HCID 86632340, compound

Product 1

HCID 57775669HCID 57775669, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of tert-butyl (3-benzyl-2-oxotetrahydrofuran-3-yl)carbamate (4.18 g, 14.3 mmol) in THF (100 mL) cooled to −78° C. was added DIBAL-H (57.4 mL, 57.4 mL, 1M hexane) dropwise over 15 min. The reaction mixture was stirred at −78° C. for 5 h, quenched with EtOAc, diluted with diethyl ether and aqueous Rochelle's salt. Vigorous stirring was allowed until gel break-up and layer formation. The organic layer was extracted, washed with aqueous Rochelle's salt, water, brine, dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography (120 g silica gel, 0 to 40% EtOAc in hexane) to give tert-butyl (3-benzyl-2-hydroxytetrahydrofuran-3-yl)carbamate (intermediate I) as a white foam (ca. 1:1 diastereomeric ratio). 1H NMR (400 MHz, CDCl3) δ 7.35-7.12 (m, 5H), 5.35 (s, 0.5H), 5.32 (s, 0.5H), 5.97 (s, 0.5H), 4.25 (s, 0.5H), 4.20-4.08 (m, 1H), 4.00-3.86 (m, 1H), 3.48-2.88 (m, 3H), 2.28-1.84 (m, 2H), 1.49 (s, 4.5H), 1.47 (s, 4.5H). MS M+Na=316.

Workup

  1. customquenched with EtOAc
  2. additiondiluted with diethyl ether and aqueous Rochelle's salt
  3. stirringVigorous stirring
  4. extractionThe organic layer was extracted
  5. washwashed with aqueous Rochelle's salt, water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography (120 g silica gel, 0 to 40% EtOAc in hexane)

Sources & evidence

ORD record
ord-5f8c040a4bac487c98b2bdf8964c016e
Source dataset
uspto-grants-2010_10
Patent number
US07816378B2

Reaction notes

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