Chloroform → N-[(S)-1-hydroxypropan-2-yl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide

HRID 1811632Notes

Reaction equation

HRID 1811632 reaction equation
C[O:2][C:3]([C@@H:5]([NH:7][C:8](=[O:33])[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][C@H:17]([NH:20][C@@H:21]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][CH:24]=3)[CH3:22])[CH2:16]2)=[CH:11][CH:10]=1)[CH3:6])=O.[BH4-].[Li+].[Cl-].[NH4+].C(Cl)(Cl)Cl>C1COCC1>[OH:2][CH2:3][C@@H:5]([NH:7][C:8](=[O:33])[C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:19][CH2:18][C@H:17]([NH:20][C@@H:21]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][CH:24]=3)[CH3:22])[CH2:16]2)=[CH:13][CH:14]=1)[CH3:6]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 58973534N-[(S)-1-methoxycarbonylethyl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide

Product 1

HCID 58973487N-[(S)-1-hydroxypropan-2-yl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamideYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 1 ml of THF was dissolved 31.9 mg of N—[(S)-1-methoxycarbonylethyl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide, 3.0 mg of lithium borohydride was added thereto, and the mixture was stirred at room temperature for 1 day. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and chloroform was added to the mixture and the mixture was stirred and then the liquids were separated. The organic layer was dried and evaporated, and then, the residue was purified by NH silica gel thin-layer chromatography (chloroform:methanol=95:5) to obtain 14.7 mg of N—[(S)-1-hydroxypropan-2-yl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide (the following Table X, Example 12.003).

Workup

  1. additionwas added
  2. additionwas added to the mixture
  3. stirringthe mixture was stirred
  4. customthe liquids were separated
  5. customThe organic layer was dried
  6. customevaporated
  7. customthe residue was purified by NH silica gel thin-layer chromatography (chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-a8c7fd485b104b4b98a82d56e04d45f6
Source dataset
uspto-grants-2013_01
Patent number
US08362274B2

Reaction notes

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