HCID 10023610, compound → (S)-6-Benzyloxy-2-methyl-hexan-1-ol

HRID 2378490Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].C([C@H]1COC(=O)N1[C:20](=[O:35])[C@@H:21]([CH3:34])[CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)C1C=CC=CC=1>C1COCC1>[CH2:27]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]([CH3:34])[CH2:20][OH:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 13.2 g (0.35 mol) of LiAlH4 in 380 ml of THF was added a solution of amide VI in 250 ml of THF at 0° C. The mixture was stirred for 2 h at 0° C. and quenched with 14 ml of H2O, 14 ml of 15% NaOH and 25 ml of H2O. The precipitated aluminum salts were removed by filtration. After concentration of the filtrate, the crude product was purified by silica gel filtration (570 g of SiO2, toluene/EtOAc=90:10, 3 l and toluene/EtOAc=80:20 1 l). The product VII was obtained as a colorless oil (54.5 g, 81% over two steps). Rf=0.24 (SiO2, 1:1 heptane-TBME); HPLC: 87% de (Chiralcel OD, n-hexane/i-PrOH=95:5, 1.0 ml/min, 30° C.) tR=10.07 min.

Workup

customquenched with 14 ml of H2O, 14 ml of 15% NaOH and 25 ml of H2O
customThe precipitated aluminum salts were removed by filtration
filtrationAfter concentration of the filtrate, the crude product was purified by silica gel filtration (570 g of SiO2, toluene/EtOAc=90:10, 3 l and toluene/EtOAc=80:20 1 l)

Sources & evidence

ORD record: ord-2ca4844275454dc7aeff16fbe04aa0b8
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470792B2

Reaction notes

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