HCID 69512394, compound → HCID 44819339, compound

HRID 1909703Notes

Reaction equation

HRID 1909703 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:29]=[CH:28][C:12]([O:13][CH2:14][C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[C:20](=O)[CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:29]=[CH:28][C:12]([O:13][CH2:14][C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 69512394HCID 69512394, compound

Product 1

HCID 44819339HCID 44819339, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-{(S)-2-[4-(4-chloro-phenyoxy)-phenoxymethyl]-pyrrolidin-1-yl}-4-oxo-butyrate (d4) (500 mg, 1 mmol, 1 eq.) in THF (14 ml) was added BH3 (1M in THF, 2 ml, 2 mmol, 2 eq.). The mixture was stirred under reflux overnight. After cooling to ambient temperature, THF was removed and the crude product was purified by chromatography on silica gel using dichloromethane as eluent to give the title product (200 mg, 49% yield).

Workup

  1. temperatureunder reflux overnight
  2. customTHF was removed
  3. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7453c74f6f4d41b79914bf25c694296d
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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