Diisobutylaluminumhydride → HCID 23571155, compound

HRID 1823986Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[C:11]([C:15]1[CH:16]=[CH:17][C:18]2[CH2:25][CH:24]3[C:26]4([CH2:30][N:29]([CH2:31][C:32]([F:35])([F:34])[F:33])[S:28](=[O:37])(=[O:36])[NH:27]4)[CH:21]([CH2:22][CH2:23]3)[CH2:20][C:19]=2[CH:38]=1)(OC)=[O:12]>O1CCCC1>[OH:12][CH2:11][C:15]1[CH:16]=[CH:17][C:18]2[CH2:25][CH:24]3[C:26]4([CH2:30][N:29]([CH2:31][C:32]([F:35])([F:33])[F:34])[S:28](=[O:37])(=[O:36])[NH:27]4)[CH:21]([CH2:22][CH2:23]3)[CH2:20][C:19]=2[CH:38]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Diisobutylaluminium hydride (1M in toluene, 49 mL, 49 mmol) was added slowly to a stirred solution of the product from Step 1 (5.1 g, 12.2 mmol) in dry tetrahydrofuran (100 mL) at −78° C. under nitrogen. After 30 minutes the reaction was allowed to warm to −10° C. and maintained at this temperature for 3 hours. The reaction was quenched with methanol and allowed to warm to room temperature. 1M Aqueous hydrochloric acid (100 mL) was added slowly. The mixture was extracted with ethyl acetate (×3). The combined organic layers were washed with brine, dried (Na2SO4) and evaporated to give a dark foam (5.2 g) which was used without further purification.

Workup

temperaturemaintained at this temperature for 3 hours
customThe reaction was quenched with methanol
temperatureto warm to room temperature
addition1M Aqueous hydrochloric acid (100 mL) was added slowly
extractionThe mixture was extracted with ethyl acetate (×3)
washThe combined organic layers were washed with brine
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-2f76c411404643ce8ffcd8c94f8eea72
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041689B2

Reaction notes

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