Lithium borohydride → 1-methylethyl {(cis)-1-acetyl-6-[4-(hydroxymethyl)-1H-imidazol-1-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate

HRID 2366949Notes

Reaction equation

HRID 2366949 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:18]=[C:17]([C:19](OCC)=[O:20])[N:16]=[CH:15]3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2].[BH4-].[Li+]>C1COCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:18]=[C:17]([CH2:19][OH:20])[N:16]=[CH:15]3)=[CH:11][CH:12]=2)[C@H:7]([NH:24][C:25](=[O:26])[O:27][CH:28]([CH3:29])[CH3:30])[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68162205ethyl 1-[(cis)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazole-4-carboxylate

Product 1

HCID 529343361-methylethyl {(cis)-1-acetyl-6-[4-(hydroxymethyl)-1H-imidazol-1-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamateYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 1-[(cis)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazole-4-carboxylate (for a preparation see Example 90) (857 mg, 2 mmol) in dry THF (10 mL) was cooled to 0° C. and treated with 2M lithium borohydride in THF (2 mL, 4 mmol). The reaction mixture was stirred at room temperature for 8 h then was partitioned between AcOEt (10 mL) and a saturated NH4Cl aqueous solution (10 mL). The layers were separated. The aqueous phase was extracted with AcOEt (2×10 mL). The combined organic phases were dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 10% MeOH in DCM) gave 1-methylethyl {(cis)-1-acetyl-6-[4-(hydroxymethyl)-1H-imidazol-1-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (440 mg, 1.139 mmol, 57%) as a colourless foam.

Workup

  1. customthen was partitioned between AcOEt (10 mL)
  2. customThe layers were separated
  3. extractionThe aqueous phase was extracted with AcOEt (2×10 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica gel (gradient: 0 to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-d8afde777d9f44ad8c838a2b0a7368da
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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