Lithium tri-s-butylborohydride → HCID 21963901, compound

HRID 2212373Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3[F:29])[CH2:16][CH2:15][C:14](=[CH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2([C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3[F:29])[CH2:16][CH2:15][CH:14]([CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -40 °C

Procedure

The product of Example 94 (150 mg, 0.32 mmol) in tetrahydrofuran (20 mL) at −40° C. was treated dropwise with L-Selectride™ (1M solution in tetrahydrofuran, 0.5 mL, 0.5 mmol). The reaction was stirred at −40° C. for 90 minutes, then quenched by the addition of ethanol (4 drops) then water (10 mL). The mixture was extracted into ethyl acetate (2×50 mL) and the combined organics washed with brine (50 mL), dried (MgSO4) and evaporated to leave a residue which was purified by flash column chromatography on silica eluting with diethyl ether:dichloromethane:iso-hexane 1:2:1, to afford the desired product (107 mg).

Workup

customquenched by the addition of ethanol (4 drops)
extractionThe mixture was extracted into ethyl acetate (2×50 mL)
washthe combined organics washed with brine (50 mL)
dry with materialdried (MgSO4)
customevaporated
customto leave a residue which
customwas purified by flash column chromatography on silica eluting with diethyl ether:dichloromethane:iso-hexane 1:2:1

Sources & evidence

ORD record: ord-1968ff89a08640ec82621f15002567b2
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101895B2

Reaction notes

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