Borohydride → HCID 86635377, compound

HRID 657180Notes

Reaction equation

HRID 657180 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]([CH2:20][CH:21]3[C:26](=O)[CH2:25][CH2:24][N:23]([CH2:28][CH2:29][N:30]4[C:39]5[C:34](=[CH:35][CH:36]=[C:37]([F:40])[CH:38]=5)[N:33]=[CH:32][C:31]4=[O:41])[CH2:22]3)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:46].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[BH4-]>ClCCl.CO>[NH2:46][CH:26]1[CH2:25][CH2:24][N:23]([CH2:28][CH2:29][N:30]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([F:40])[CH:38]=3)[N:33]=[CH:32][C:31]2=[O:41])[CH2:22][CH:21]1[CH2:20][N:12]([CH2:11][C:8]1[N:7]=[CH:6][C:5]2[O:4][CH2:3][CH2:2][O:1][C:10]=2[CH:9]=1)[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 28123BorohydrideHCID 517165Ammonium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 69185297HCID 69185297, compound

Product 1

HCID 86635377HCID 86635377, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)({1-[2-(7-fluoro-2-oxo-1(2H)-quinoxalinyl)ethyl]-4-oxo-3-piperidinyl}methyl)carbamate (0.23 g, 0.41 mmol) and ammonium acetate (0.31 g, 4.1 mmol) in 1:1 dichloromethane/methanol (10 mL) was stirred for 4 h before addition of sodium triacetoxyborohydride (0.53 g, 2.5 mmol). Stirring was continued over two nights, with further additions of borohydride (as above) after the first overnight period, and again after another 7 h. Basification with sodium bicarbonate, extraction with 10% methanol/dichloromethane, evaporation of the organic fractions and chromatography on silica, eluting with 0-20% (2M ammonia/methanol)/dichloromethane, gave the product (0.11 g, 47%).

Workup

  1. extractionBasification with sodium bicarbonate, extraction
  2. customwith 10% methanol/dichloromethane, evaporation of the organic fractions and chromatography on silica
  3. washeluting with 0-20% (2M ammonia/methanol)/dichloromethane

Sources & evidence

ORD record
ord-d75da6eebb1e432bbf6c8752d28b2261
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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