Methanol → HCID 178519590, compound

HRID 2080951Notes

Reaction equation

HRID 2080951 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][C:19](OC)=[O:20])[CH2:14][CH2:13]2)[CH:9]2[CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1.[BH4-].[Li+].CO>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]([CH:9]2[CH2:10][CH2:11]2)[C@H:12]2[CH2:13][CH2:14][C@H:15]([CH2:18][CH2:19][OH:20])[CH2:16][CH2:17]2)=[O:7])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 178500700HCID 178500700, compound

Product 1

HCID 178519590HCID 178519590, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(trans-4-(4-chloro-N-cyclopropylbenzamido)cyclohexyl)acetate (0.182 g, 0.52 mmol) in THF (3 mL) was added lithium borohydride (2 M solution in THF, 3.5 ml) and MeOH (0.5 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then quenched with saturated NH4Cl (10 mL) and extracted with EtOAc twice. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude product was purified through silica gel chromatography eluting with 5% MeOH—CH2Cl2. The desired alcohol product was obtained as a white solid (0.115 g). MS: 322 (M+1), C18H24ClNO2.

Workup

  1. customThe reaction mixture was then quenched with saturated NH4Cl (10 mL)
  2. extractionextracted with EtOAc twice
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified through silica gel chromatography
  6. washeluting with 5% MeOH—CH2Cl2

Sources & evidence

ORD record
ord-d5be7720707448738846c9985041429a
Source dataset
uspto-grants-2011_04
Patent number
US07932421B2

Reaction notes

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