Sodium borohydride → HCID 68877648, compound

HRID 1787842Notes

Reaction equation

HRID 1787842 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH:19]([OH:40])[CH2:20][NH:21][C:22]([CH3:39])([CH3:38])[CH2:23][CH2:24][N:25]2[CH:29]=[CH:28][N:27]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[CH2:26]2)=[CH:15][C:10]=1[C:11](OC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>O1CCCC1.C(O)C>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH:19]([OH:40])[CH2:20][NH:21][C:22]([CH3:39])([CH3:38])[CH2:23][CH2:24][N:25]2[CH:29]=[CH:28][N:27]([C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[CH2:26]2)=[CH:15][C:10]=1[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydride2×HCID 5284359Calcium Chloride2×HCID 68877168HCID 68877168, compound

Product 1

HCID 68877648HCID 68877648, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

13 g of methyl 2-benzyloxy-5-(1-hydroxy-2-{3-[3-(4-methoxy-phenyl)-imidazol-1-yl]-1,1-dimethyl-propylamino}-ethyl)-benzoate in 100 mL tetrahydrofuran are reacted with a solution of 6.5 g of calcium chloride in 65 mL ethanol and 4.5 g of sodium borohydride analogously to the method used for Example 1c. After a reaction time of 12 hours, 3 g of calcium chloride, dissolved in 30 mL ethanol, and 2 g of sodium borohydride are added and stirring is continued for a further 12 hours. Then the mixture is worked up as described, except that extraction is carried out using chloroform rather than ethyl acetate. During the evaporation of this organic phase a solid is precipitated out. The solid is suction filtered, stirred with ethyl acetate and recrystallised from acetonitrile. Yield: 79.5 g (77%); m.p.=108-111° C.

Workup

  1. extractionas described, except that extraction
  2. customDuring the evaporation of this organic phase a solid
  3. customis precipitated out
  4. filtrationfiltered
  5. stirringstirred with ethyl acetate
  6. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-0b6542bca0fa4b02977893324d8e1da7
Source dataset
uspto-grants-2009_03
Patent number
US07511067B2

Reaction notes

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