HCID 10753483, compound → HCID 15511797, compound

HRID 987998Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][C:9](=[O:12])[C:8]2[N:13]([CH3:16])[CH:14]=[CH:15][C:7]=2[C:6]1=[O:17]>C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][C@H:9]([OH:12])[C:8]2[N:13]([CH3:16])[CH:14]=[CH:15][C:7]=2[C:6]1=[O:17]

Participants

Conditions

Temperature: -8 °C

Procedure

17.2 mg (0.03 mmol; 0.3 mol %) of optically active cobalt (II) complex of the formula (VIII) and 2.54 g (10.0 mmol) of 5-(3-chloropropyl)-1-methyl-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]-azepine-4,8-dione were added in a second reactor, then the atmosphere was replaced with a nitrogen gas, and the mixture was dissolved in 100 mL of THF. To this mixture was added the reducing reagent prepared in process (a) dropwise at −8° C. of reaction bath temperature and the reaction mixture was stirred for 3 hours at −8° C. The reaction mixture was washed with a mixed solution of 40 mL of saturated saline solution and 8 mL of water, and further washed with 40 mL of saturated saline solution, and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 6.16 g (optical purity: 83.5% e.e.) of (S)-5-(3-chloropropyl)-8-hydroxy-1-methyl-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]azepin-4-one as pale brown crystalline.

Workup

additionTo this mixture was added the reducing reagent
washThe reaction mixture was washed with a mixed solution of 40 mL of saturated saline solution and 8 mL of water
washfurther washed with 40 mL of saturated saline solution
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-571db811faf343a095043c9664f7bfda
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632943B2

Reaction notes

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