Lithium borohydride → HCID 67074127, compound

HRID 2095540Notes

Reaction equation

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

Participants

Reactant 2

HCID 4148881Lithium borohydride

HCID 67074060HCID 67074060, compound2×

Product 1

HCID 67074127HCID 67074127, compoundYield 84%

Procedure

In analogy to the procedure described in example 6B, 2-{4-[(E)-3-(3-chloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-succinic acid 4-tert-butyl ester 1-methyl ester (intermediate 8C) and 2 eq. of LiBH4 gave, after only 1 night of stirring and purification on a SiO2-column (dichloromethane/MeOH 98:2-95:5), the titled compound in 84% yield as white foam. MS: 436.9 (MH+, 1Cl).

Workup

customgave, after only 1 night
custompurification on a SiO2-column (dichloromethane/MeOH 98:2-95:5)

Sources & evidence

ORD record: ord-fed36d82712647fda9ac3589b0880b34
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445674B2

Reaction notes

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