Diisobutylaluminum hydride → HCID 178521036, compound

Temperature

-78 °C

In a 50 mL flask with cis-3-benzyloxymethyl-cyclobutanecarbaldehyde (73 mg, 0.36 mmol) inside, dry CH2Cl2 7 mL was added under argon to give a colorless solution. Then this was cooled to −78° C., DIBAL-H (1.0 M in hexane, 0.7 mL, 0.72 mmol) was added drop by drop. This was left stirring at −78° C. and after 3 hr, the reaction was quenched with dry MeOH 0.2 mL. The reaction mixture was allowed to warm up to RT gradually. After 1.5 hr, 2 mL Rochelle salt was added and the mixture was stirred vigorously for overnight. Then the organic phase was separated and washed with brine, dried over MgSO4 and concentrated. Purification by silica gel flash chromatography (Hexane:EtOAc=3:1) yielded cis-1-hydroxymethyl-3-benzyloxymethyl-cyclobutane as a colorless oil (54 mg, 73.4%, Rf=0.17 (Hexane: EtOAc=3:1)). 1H NMR (CDCl3, 300 MHz): δ 1.48-1.61 (m, 2H), 2.10-2.20 (m, 2H), 2.40-2.55 (m, 2H), 3.39-3.41 (d, J=8.0, 2H), 3.54-3.56 (d, J=8.0, 2H), 4.51 (s, 2H), 7.20-7.40 (m, 5H).

1. customto give a colorless solution
2. waitThis was left
3. customthe reaction was quenched with dry MeOH 0.2 mL
4. temperatureto warm up to RT gradually
5. waitAfter 1.5 hr
6. addition2 mL Rochelle salt was added
7. stirringthe mixture was stirred vigorously for overnight
8. customThen the organic phase was separated
9. washwashed with brine
10. dry with materialdried over MgSO4
11. concentrationconcentrated
12. customPurification by silica gel flash chromatography (Hexane:EtOAc=3:1)

ORD record

ord-9d59dee777994a47bcdae1b09a2e3386

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07495006B2