Sodium borohydride → HCID 18784723, compound

HRID 1418729Notes

Reaction equation

HRID 1418729 reaction equation
Cl.[O:2]=[C:3]([C:23]1([CH2:36][CH2:37][CH3:38])[C:35]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([N:13]2[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:22])[CH2:9][CH2:8]1.[BH4-].[Na+]>CO.ClCCl>[OH:2][CH:3]([C:23]1([CH2:36][CH2:37][CH3:38])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=2[C:30]2[C:35]1=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([N:13]2[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:22])[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 131720604HCID 131720604, compound

Product 1

HCID 18784723HCID 18784723, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 311 Part D free amine (300 mg, 0.61 mmol) in 12 ml of methanol was cooled to 0° C. under an argon atmosphere and 2 equiv. of sodium borohydride (48.5 mg, 1.28 mmol) was added. The reaction mixture was stirred at 0° C. for 45 min. The reaction was quenched with 1N hydrochloric acid and extracted with ethyl acetate (3×20 ml). The extract was washed with brine and dried over sodium sulfate. Evaporation yielded an oily residue which was dissolved in dichloromethane, dried over sodium sulfate and evaporated to yield 550 mg of a colorless solid. The crude product was purified on a Merck EM silica column eluting with 5% methanol/dichloromethane yielding 290mg (96%) of title compound as colorless solid.

Workup

  1. customThe reaction was quenched with 1N hydrochloric acid
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation
  6. customyielded an oily residue which
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-194a914a83fe4e828e519c0aae44298c
Source dataset
uspto-grants-1999_03
Patent number
US05883099

Reaction notes

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