Water → Benzyl 3-hydroxycyclohexane-1-carboxylate

HRID 340772Notes

Reaction equation

CC(C1NC(=O)C(CCSC)NC(=O)C(NC(C(NC(C(NC(C(NC(C(N)CC(O)=O)=O)C(O)C)=O)CCSC)=O)CCCNC(N)=N)=O)CSSCC(C(NC(C(NC(C(NC(C(O)=O)C(C)C)=O)CCC(O)=O)=O)CC2C3C(=CC=CC=3)NC=2)=O)NC(=O)C2N(CCC2)C(=O)C(CCCNC(N)=N)NC(=O)C(C[C:128]2[CH:133]=[CH:132][C:131]([OH:134])=[CH:130][CH:129]=2)NC(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC1=O)C.[BH4-].[Na+].[OH2:147].[CH2:148]1[CH2:152][O:151][CH2:150][CH2:149]1>CCOCC>[OH:134][CH:131]1[CH2:130][CH2:129][CH2:128][CH:133]([C:150]([O:151][CH2:152][C:148]2[CH:149]=[CH:130][CH:129]=[CH:128][CH:133]=2)=[O:147])[CH2:132]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of benzyl 3-oxocyclohexanecarboxylate 1 (2.50 g, 10.8 mmol) in 55 mL of THF was added NaBH4 (814 mg, 21.5 mmol) portionwise. The reaction mixture was maintained at 0° C. for 20 min. Then water was slowly added to the reaction, and the reaction was diluted with Et2O. The resulting layers were separated and the aqueous layer was further extracted with Et2O. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. Purification of the resulting residue by flash chromatography (Biotage™ 40M 5-25% EtOAc/hexanes then 25-35% EtOAc/hexanes) afforded the title compound as a clear, colorless oil. LCMS: calculated for C14H18O3 234.29, observed m/e 235.0 (M+H)+ 256.9 (M+Na) (Rt 1.74/4 min).

Workup

customThe resulting layers were separated
extractionthe aqueous layer was further extracted with Et2O
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customPurification of the resulting residue by flash chromatography (Biotage™ 40M 5-25% EtOAc/hexanes

Sources & evidence

ORD record: ord-0018eef19c5f44878ebcf8d0f9b3c558
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895596B2

Reaction notes

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