rac-tert-butyl N-[(1r,4r)-4-formylcyclohexyl]carbamate → HCID 178453952, compound

HRID 1012934Notes

Reaction equation

[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[C:6]([O:10][C:11](=[O:21])[NH:12][CH:13]1[CH2:18][CH2:17][CH:16]([CH:19]=[O:20])[CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7]>C1COCC1>[C:6]([O:10][C:11](=[O:21])[NH:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([CH:19]([C:11]2[O:10][C:1]3[CH:3]=[CH:8][CH:6]=[CH:7][C:2]=3[N:12]=2)[OH:20])[CH2:17][CH2:18]1)([CH3:9])([CH3:7])[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-methoxy-benzoxazole (1490 mg, 10 mmol, obtained by methylation of 4-hydroxybenzoxazole (J. Med. Chem. (1987), 30, 62) in THF (60 ml) was added dropwise a solution of i-PrMgCl (5 ml, 2M solution in THF). The red mixture was stirred at 0° C. for 1 h before dropwise addition of (4-formyl-cyclohexyl)-carbamic acid tert-butyl ester (1360 mg, 6 mmol) dissolved in THF (10 ml). The reaction was stirred at 0° C. for 30 min and at RT for 1 h. The reaction mixture was quenched with aq. ammonium chloride solution and extracted EtOAc. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by chromatograpy on SiO2 (hex/EtOAc 2:1, 1:1) affording 1300 mg (59%) of product as yellow oil.

Workup

customThe reaction mixture was quenched with aq. ammonium chloride solution
extractionextracted EtOAc
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatograpy on SiO2 (hex/EtOAc 2:1, 1:1)

Sources & evidence

ORD record: ord-224b7b1dd67747119c89f1bd51dc1334
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981886B2

Reaction notes

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