Lithium borohydride → HCID 21701984, compound

HRID 1596453Notes

Reaction equation

HRID 1596453 reaction equation
[Li+].[BH4-].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([CH2:14][CH2:15][N:16]2[CH2:23][CH:22]3[CH2:24][CH:18]([CH2:19][N:20]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]3)[CH2:17]2)=O)=[CH:7][CH:6]=1)#[N:4]>C1(C)C=CC=CC=1.C1COCC1>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][CH2:12][CH2:14][CH2:15][N:16]2[CH2:17][CH:18]3[CH2:24][CH:22]([CH2:21][N:20]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[CH2:19]3)[CH2:23]2)=[CH:9][CH:10]=1)#[N:4]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 54492309HCID 54492309, compound

Product 1

HCID 21701984HCID 21701984, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiBH4 (300 mg; 13.6 mmol) was added to a stirred solution of tert-butyl 7-{2-[(4-cyanophenyl)carbamoyl]ethyl}-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (1.36 g; 3.41 mmol; see Example 22 above) in toluene (10 mL) and THF (5 mL) and the reaction mixture was stirred for 45 min. The solvents were removed and the residue partitioned between DCM and NaHCO3 (aq.). The organic layer was concentrated and subjected to column chromatography (DCM:MeOH; 9:1) to give the title compound in a 10% yield.

Workup

  1. customThe solvents were removed
  2. customthe residue partitioned between DCM and NaHCO3 (aq.)
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-464d55ee87ad4a4f97512ba813ed5af3
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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