Sodium triacetoxyborohydride → HCID 178453893, compound

HRID 72853Notes

Reaction equation

HRID 72853 reaction equation
Cl.[Cl:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.[C:18]([O:22][C:23](=[O:34])[NH:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([CH2:31][CH:32]=O)[CH2:27][CH2:26]1)([CH3:21])([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:18]([O:22][C:23](=[O:34])[NH:24][C@H:25]1[CH2:26][CH2:27][C@H:28]([CH2:31][CH2:32][N:13]2[CH2:12][CH2:11][CH:10]([C:7]3[C:6]4[CH:16]=[CH:17][C:3]([Cl:2])=[CH:4][C:5]=4[O:9][N:8]=3)[CH2:15][CH2:14]2)[CH2:29][CH2:30]1)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 1307643184163-18-8HCID 178453924HCID 178453924, compound

Product 1

HCID 178453893HCID 178453893, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Prepared as described for intermediate F (example 1) from a mixture 6-Chloro-3-piperidin-4-yl-benzo[d]isoxazole hydrochloride (0.942 g, 4 mmol), trans-[4-(2-Oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (1.06 g, 4 mmol) and sodium triacetoxyborohydride (1.51 g, 7 mmol) in 1,2 dichloroethane (9.8 mL) The product fractions were concentrated to give 1.2 g (2.6 mmol, 64.3% yield) of a light brown solid. MS (m/e): 462.4 (M+H+).

Workup

  1. customPrepared
  2. concentrationwere concentrated

Sources & evidence

ORD record
ord-ef099d73f64c4ec989140bd9125cc6b8
Source dataset
uspto-grants-2014_09
Patent number
US08829029B2

Reaction notes

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