Acetic Anhydride → HCID 15946647, compound

HRID 558022Notes

Reaction equation

HRID 558022 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:11][C@H:10]([CH2:12][P:13]([O:18][CH2:19][CH3:20])(=[O:17])[O:14][CH2:15][CH3:16])[C@@H:9]([N:21]=[N+]=[N-])[C@@H:8]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:7]1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:3])[CH3:2].[BH4-].[Na+].[CH3:42][C:43](OC(C)=O)=[O:44]>CO.C1(C)C=CC=CC=1.Cl[Ni]Cl>[C:1]([O:4][CH2:5][C@H:6]1[O:11][C@H:10]([CH2:12][P:13]([O:18][CH2:19][CH3:20])(=[O:17])[O:14][CH2:15][CH3:16])[C@@H:9]([NH:21][C:43](=[O:44])[CH3:42])[C@@H:8]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:7]1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 4311764Sodium borohydrideHCID 15946646HCID 15946646, compound

Product 1

HCID 15946647HCID 15946647, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of 4 (2.50 g, 4.45 mmol) in MeOH (125 mL) a catalytic amount of NiCl2×6H2O was added followed by portions of NaBH4 (in total 0.34 g, 8.9 mmol) every 10 min until no starting material was observed on TLC (system). Ac2O (3 mL) was added after 50 min and the reaction mixture was diluted with toluene, filtered through a plug of silica and concentrated. The residue was purified by silica gel chromatography to give 5 (1.95 g, 3.4 mmol, 76%). 13C-NMR (CDCl3) 170.4, 169.7, 137.3, 137.0 remaining aromatic C 128.5-127.7, 75.3, 72.6, 72.4, 72.1, 72.0, 67.1, 61.91, 61.8, 61.8, 61.3, 61.2, 48.8, 48.6, 28.5 (d, J=142 Hz), 23.0, 20.6, 16.3, 16.2, 16.1; 31P-NMR (CDCl3) 29.5.

Workup

  1. filtrationfiltered through a plug of silica
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d9f03763e2064d2184e3cc19c48d6cdb
Source dataset
uspto-grants-2011_11
Patent number
US08062641B2

Reaction notes

Loading…