Diisobutylaluminumhydride → HCID 10514391, compound

HRID 654317Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:10](=[O:13])[CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[C@H:10]([OH:13])[CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of the resultant compound of Example 30 (3.25 g, 14.4 mmol) in anhydrous tetrahydrofuran was cooled to -78° C. and treated slowly along the side of the reaction vessel with 57 ml (57 mmol) of diisobutylaluminum hydride (1M in tetrahydrofuran). The solution was stirred at -78° C. for 0.5 h, quenched cautiously with methanol, allowed to warm to ambient temperature, and partitioned between ether and aqueous Rochelle salts. The organic phase was washed sequentially with water and brine, dried over MgSO4, and concentrated in vacuo. Chromatography on silica gel using 4:1 hexane:ethyl acetate provided 0.77 g (22%) of the desired compound (10:1 ratio of (3S,4S):(3R:4S) isomers). 1H NMR (CDCl3) δ 0.91 (d, J=7 Hz 3 H), 0.94 (d, J=7 Hz, 3 H), 1.26 (br t, J=7 Hz, 2 H), 1.44 (s, 9 H), 1.67 (nonet J=7 Hz, 1 H), 2.96 (br d, J=5 Hz, 1 H), 3.82 (m, 1 H), 4.18 (m, 1 H), 4.50 (br d, 1 H), 5.23 (dt, J=11, 1.5 Hz, 1 H), 5.33 (dt, J=17, 1.5 Hz, 1 H), 5.84 (ddd, J=17, 11, 6 Hz, 1 H).

Workup

customquenched cautiously with methanol
temperatureto warm to ambient temperature
custompartitioned between ether and aqueous Rochelle salts
washThe organic phase was washed sequentially with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-befa375f797e4634b048111779e23cd6
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05130468

Reaction notes

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