Ammonium Chloride → HCID 59853923, compound

HRID 2374858Notes

Reaction equation

HRID 2374858 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:21]([N:23]1[CH2:28][CH2:27][C:26](=[C:29]2[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[CH:33]=[CH:32][C:31]3[CH:40]=[CH:41][CH:42]=[CH:43][C:30]2=3)[CH2:25][CH2:24]1)=[O:22])[CH2:10][C:11](OCC1C=CC=CC=1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[CH:39]1[C:34]2[CH:33]=[CH:32][C:31]3[CH:40]=[CH:41][CH:42]=[CH:43][C:30]=3[C:29](=[C:26]3[CH2:25][CH2:24][N:23]([C:21]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][CH2:11][OH:12])=[O:22])[CH2:28][CH2:27]3)[C:35]=2[CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 69232941HCID 69232941, compoundHCID 131718764lithium borohydride THF

Product 1

HCID 59853923HCID 59853923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

797 mg (1.38 mmol) of benzyl (S)-3-[(tert-butoxycarbonyl)amino]-4-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-4-oxobutanoate was dissolved in 15 ml of tetrahydrofuran. 1.45 ml of 2 M lithium borohydride/tetrahydrofuran solution was added to the obtained solution in argon atmosphere at 0° C., and they were stirred at room temperature overnight. Saturated aqueous ammonium chloride solution was added to the reaction mixture under cooling with ice. After extracting with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by the silica gel chromatography (hexane:ethyl acetate=3:1 to 1:1) to obtain the title compound.

Workup

  1. temperatureunder cooling with ice
  2. extractionAfter extracting with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by the silica gel chromatography (hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-941a2db658814336a6ec1569be7260b0
Source dataset
uspto-grants-2008_12
Patent number
US07462630B2

Reaction notes

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