Methanol → HCID 178439172, compound

HRID 2080953Notes

Reaction equation

HRID 2080953 reaction equation
[CH:1]1([N:4]([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][C:23](OC)=[O:24])[CH2:18][CH2:17]2)[C:5](=[O:15])[C:6]2[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[BH4-].[Li+].CO>C1COCC1>[CH:1]1([N:4]([C@H:16]2[CH2:17][CH2:18][C@H:19]([CH2:22][CH2:23][OH:24])[CH2:20][CH2:21]2)[C:5](=[O:15])[C:6]2[CH:11]=[CH:10][C:9]([CH:12]([CH3:13])[CH3:14])=[CH:8][CH:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydride2×HCID 178500698HCID 178500698, compound

Product 1

HCID 178439172HCID 178439172, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(trans-4-(N-cyclopropyl-4-isopropylbenzamido)cyclohexyl)acetate (0.100 g, 0.28 mmol) in THF (3 mL) was added lithium borohydride (2 M solution in THF, 0.14 mL, 0.28 mmol) at 0° C. The reaction mixture was checked after being stirred overnight. HPLC-MS showed product and starting material. More lithium borohydride (0.14 mL) (2 M solution in THF) and MeOH (0.1 mL) were added to the mixture. After being stirred overnight, the reaction mixture was quenched with saturated NH4Cl (10 mL) and then extracted with EtOAc twice. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel chromatography eluting with 55% EtOAc-hexane. The alcohol product was obtained as a sticky white solid (80 mg). MS: 330 (M+1), C2131NO2.

Workup

  1. stirringAfter being stirred overnight
  2. customthe reaction mixture was quenched with saturated NH4Cl (10 mL)
  3. extractionextracted with EtOAc twice
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with 55% EtOAc-hexane

Sources & evidence

ORD record
ord-5be2757070c6400ea65aad1ea7cbc271
Source dataset
uspto-grants-2011_04
Patent number
US07932421B2

Reaction notes

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