Lithium borohydride → HCID 86754741, compound

HRID 1601035Notes

Reaction equation

HRID 1601035 reaction equation
[ClH:1].Cl.[C:3]([C@@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)[CH2:10][N:9]1[CH2:24][C:25]1[N:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=2)[CH:28]=[N:27][CH:26]=1)(OCC)=[O:4].[Li+].[BH4-]>C1COCC1>[ClH:1].[ClH:1].[OH:4][CH2:3][C@@H:8]1[CH2:17][C:16]2[C:11](=[CH:12][C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:14][CH:15]=2)[CH2:10][N:9]1[CH2:24][C:25]1[N:29]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:37]#[N:38])=[CH:35][CH:36]=2)[CH:28]=[N:27][CH:26]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67598441HCID 67598441, compound

Product 1

HCID 86754741HCID 86754741, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

3(S)-Carboethoxy-7-phenyl-2-(1-(4-cyanobenzyl)-5-imidazolylmethyl)-1,2,3,4-tetrahydroisoquinoline (150 mg, 0.32 mmol) from Example 21 was dissolved in THF (3 mL) and treated with LiBH4 (13.7 g, 0.64 mmol). The solution was heated at 50° C. for 3 h then quenched with 1N HCl and extracted with EtOAc (3×), washed with brine, dried and evaporated. The residue was purified by preparative HPLC (gradient elution with water/acetonitrile containing 0.1% TFA), the product neutralized and converted to the HCl salt using 1N HCl in ether to give the title compound as a white solid.

Workup

  1. customthen quenched with 1N HCl
  2. extractionextracted with EtOAc (3×)
  3. washwashed with brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by preparative HPLC (gradient elution with water/acetonitrile containing 0.1% TFA)

Sources & evidence

ORD record
ord-2fdd75bcd6f34859918bd61378aac4eb
Source dataset
uspto-grants-1999_11
Patent number
US05977134

Reaction notes

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