Sodium triacetoxyborohydride → HCID 67317121, compound

HRID 1013822

Reaction equation

HRID 1013822 reaction equation
C([C@@H]1COC(=O)N1[C:14](=[O:36])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:22][C:21]=1[Cl:35])[CH2:16][CH:17]=O)C1C=CC=CC=1.[NH:37]1[C:45]2[CH2:44][CH:43]([NH2:46])[CH2:42][CH2:41][C:40]=2[CH:39]=[N:38]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(#N)C>[CH2:28]([O:27][C:23]1[CH:22]=[C:21]([Cl:35])[C:20]([CH2:19][C@@H:15]2[CH2:16][CH2:17][N:46]([CH:43]3[CH2:44][C:45]4[NH:37][N:38]=[CH:39][C:40]=4[CH2:41][CH2:42]3)[C:14]2=[O:36])=[C:25]([Cl:26])[CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 128984204,5,6,7-tetrahydro-1H-indazol-6-amineHCID 59515429(R)-4-((R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde

Product 1

HCID 67317121HCID 67317121, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Add a solution of (R)-4-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde, Preparation 38, (8.17 g, 15.5 mmol) in CH2Cl2 (100 mL) to a solution of 4,5,6,7-tetrahydro-1H-indazol-6-ylamine (2.13 g, 15.5 mmol) in acetonitrile (200 mL) and stir for 30 minutes at room temperature under N2. Add sodium triacetoxyborohydride (9.89 g, 46.7 mmol) to the reaction and stir for 18 hours. Remove the solvent in vacuo and extract solid with ethyl acetate, water and saturated NaHCO3. Dry the organic layer (Na2SO4), filter and concentrate under vacuum. Purify the residue by silica gel chromatography with a gradient of 0 to 10% methanol in CH2Cl2 to afford 3.93 g (54%) of the title compound. MS (m/z): 470 (M+).

Workup

  1. additionAdd
  2. stirringstir for 18 hours
  3. customRemove the solvent in vacuo
  4. extractionextract solid with ethyl acetate, water and saturated NaHCO3
  5. dry with materialDry the organic layer (Na2SO4)
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by silica gel chromatography with a gradient of 0 to 10% methanol in CH2Cl2

Sources & evidence

ORD record
ord-94f60d92b451432b85aa7e1333db4d8c
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Linked notes

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