Lithium borohydride → HCID 15818078, compound

HRID 1419594Notes

Reaction equation

HRID 1419594 reaction equation
[BH4-].[Li+].[CH2:3]([NH:10][C@@H:11]([CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=1)[C:12]([N:14]1[CH2:19][CH2:18][C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:20](OC)=[O:21])[CH2:16][CH2:15]1)=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1(C)C=CC=CC=1.O1CCCC1>[CH2:3]([NH:10][C@@H:11]([CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[CH:34]=1)[C:12]([N:14]1[CH2:19][CH2:18][C:17]([CH2:20][OH:21])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:16][CH2:15]1)=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 15818077HCID 15818077, compound

Product 1

HCID 15818078HCID 15818078, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (5.0 mg) was added to a stirred solution of (S)-methyl 1-[2-benzylamino-3-(3,4-dichlorobenzyloxy)propionyl]-4-phenylpiperidin-4-carboxylate (100 mg) in toluene (5.0 mL) and tetrahydrofuran (5.0 mL). The resulting solution was warmed to reflux for 3 h., cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and aqueous ammonium chloride (saturated) and the organic layer was separated, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by MPLC on silica gel, eluting with CH2Cl2 /MeOH/NH3 (Aq.) (99:1:0.1) to give the title compound as a colorless solid (26 mg), δH (CDCl3) 1.69-1.82 (5H, m), 2.41-2.61 (4H, m), 3.15-3.21 (2H m), 3.44 (2H, s), 3.53-3.68 (4H, m), 4.34 (1H br s), 6.98-7.46 (12H, m). m/e (ES+) 527 (MH+).

Workup

  1. temperatureThe resulting solution was warmed
  2. temperatureto reflux for 3 h.
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and aqueous ammonium chloride (saturated)
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by MPLC on silica gel
  9. washeluting with CH2Cl2 /MeOH/NH3 (Aq.) (99:1:0.1)

Sources & evidence

ORD record
ord-122e9c87cb20452282899b5d1a22bc6f
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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