Potassium;tri(butan-2-yl)boranuide → HCID 69890663, compound

HRID 2088109Notes

Reaction equation

CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[C:15]([C@@H:17]1[CH2:23][C@:22]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:24]([CH2:25][CH:26]=[CH2:27])[C@H:18]1[CH:19]=[CH:20][C:21]2=[O:34])#[N:16]>C1COCC1>[C:15]([C@@H:17]1[CH2:23][C@:22]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:24]([CH2:25][CH:26]=[CH2:27])[C@H:18]1[CH2:19][CH2:20][C@H:21]2[OH:34])#[N:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of K-Selectride® in THF (1M, 20 ml, 20 mmol) was added dropwise to a stirred solution of (1R*,5S*,6R*)-6-cyano-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]oct-3-en-2-one (Description 23a; 1.6 g, 6 mmol) in THF (20 ml) at −70° C. The reaction mixture was slowly warm up to 0° C. over 90 minutes and carefully quenched with a mixture of 2M NaOH (40 ml) and H2O2 (35%, 10 ml). The mixture was stirred for 15 minutes and extracted into dichloromethane (3×100 ml). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate 0-4%) to give the title compound (1.1 g, 68%).

Workup

customcarefully quenched with a mixture of 2M NaOH (40 ml) and H2O2 (35%, 10 ml)
extractionextracted into dichloromethane (3×100 ml)
dry with materialThe combined organic extracts were dried (Na2SO4)
concentrationconcentrated
customThe residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate 0-4%)

Sources & evidence

ORD record: ord-82a4428a5ea141d1903b82242ca809a2
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727249B2

Reaction notes

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