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Water → Benzyl 3-hydroxycyclohexane-1-carboxylate

HRID 340772
Notes
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Reaction equation

HRID 340772 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 16167454Melanin-concentrating hormone

Product 1

HCID 14296104Benzyl 3-hydroxycyclohexane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

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

  1. customThe resulting layers were separated
  2. extractionthe aqueous layer was further extracted with Et2O
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes