Sodium borohydride → HCID 18784723, compound

HRID 1108530Notes

Reaction equation

HRID 1108530 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 1 N 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 290 mg (96%) of title compound as colorless solid.

Workup

  1. customThe reaction was quenched with 1 N 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-42a45a15e3c6413c9c08f677a246104a
Source dataset
uspto-grants-2000_05
Patent number
US06066650

Reaction notes

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