Diisobutylaluminumhydride → HCID 66859901, compound

HRID 1696852Notes

Reaction equation

HRID 1696852 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C@@H:10]([OH:38])[CH2:11][NH:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])=[CH:19][CH:18]=2)[CH:7]=[CH:6][C:5]=1[O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[CH2:31]([O:30][C:28](=[O:29])[NH:27][CH2:26][CH2:25][CH2:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH2:15][CH2:14][CH2:13][NH:12][CH2:11][C@@H:10]([C:8]2[CH:7]=[CH:6][C:5]([O:39][CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[C:4]([CH2:3][OH:2])[CH:9]=2)[OH:38])=[CH:18][CH:19]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 66860879HCID 66860879, compound

Product 1

HCID 66859901HCID 66859901, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 60 (0.62 g, 0.97 mmol) dissolved in anhydrous tetrahydrofuran (6 as cooled to 0° C. The solution was treated with diisobutylaluminum hydride (4.8 mL, 1M in hexanes). The reaction mixture was allowed to slowly warm to room temperature over 16 h. The solution was concentrated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane to afford the desired product 61 (0.38 g, 64%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 7.43 (s, 4H), 7.40-7.17 (m, 10H), 7.07 (s, 2H), 6.97 (dd, 1H), 5.12 (s, 2H), 5.04 (s, 2H), 4.78 (dd, 1H), 4.69 (d, 2H), 3.63 (t, 2H), 3.11 (t, 2H), 2.62-2.46 (m, 6H), 1.61 (br, 4H), 1.51 (br, 2H); m/z (ESI) 611 [C38H46N2O5+H]+.

Workup

  1. temperatureto slowly warm to room temperature over 16 h
  2. concentrationThe solution was concentrated in vacuo
  3. customThe resulting residue was purified by column chromatography
  4. washeluting with a mixture of 0-20% (10% concentrated ammonium hydroxide in methanol) and dichloromethane

Sources & evidence

ORD record
ord-73c5667efbb044d796ca00e404abc973
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

Loading…