Lithium borohydride → HCID 52913249, compound

HRID 2095595Notes

Reaction equation

HRID 2095595 reaction equation
C[O:2][C:3](=O)[C@@H:4]([N:18]1[C:24](=[O:25])[CH2:23][CH2:22][N:21]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[C:28]([Cl:36])[CH:27]=2)[CH2:20][CH2:19]1)[CH2:5][CH2:6][C:7]([N:9]1[CH2:16][CH2:15][C:12]2([CH2:14][CH2:13]2)[C@H:11]([OH:17])[CH2:10]1)=[O:8].[Li+].[BH4-]>CO>[Cl:36][C:28]1[CH:27]=[C:26]([N:21]2[CH2:22][CH2:23][C:24](=[O:25])[N:18]([C@H:4]([CH2:3][OH:2])[CH2:5][CH2:6][C:7]([N:9]3[CH2:16][CH2:15][C:12]4([CH2:13][CH2:14]4)[C@H:11]([OH:17])[CH2:10]3)=[O:8])[CH2:19][CH2:20]2)[CH:31]=[CH:30][C:29]=1[C:32]([F:34])([F:35])[F:33]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 58232206HCID 58232206, compound

Product 1

HCID 52913249HCID 52913249, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In analogy to the procedure described for intermediate 40C, (S)-2-[4-(3-Chloro-4-trifluoromethyl-phenyl)-7-oxo-[1,4]diazepan-1-yl]-5-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-5-oxo-pentanoic acid methyl ester (example 123) and LiBH4 (2 M in THF)/MeOH gave the title compound in 62% yield as yellow oil. MS: 518.20 (MH+, Cl).

Sources & evidence

ORD record
ord-64deebba43d249feb6791eab62752105
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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