4-Chlorobenzaldehyde → HCID 86690406, compound

HRID 513906Notes

Reaction equation

HRID 513906 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:36])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:35])[CH2:12][CH2:13][C@@:14]3([C@H:31]([OH:34])[CH2:32][NH2:33])[CH2:26][C:25](=[O:27])[C:24]([CH:28]([CH3:30])[CH3:29])=[C:15]32)[C:6]1([CH3:38])[CH3:37])(=[O:3])[CH3:2].C(N(CC)CC)C.S([O-])([O-])(=O)=O.[Mg+2].[Cl:52][C:53]1[CH:60]=[CH:59][C:56]([CH:57]=O)=[CH:55][CH:54]=1.[BH4-].[Na+]>CO>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@:10]3([CH3:36])[C@@H:19]2[CH2:18][CH2:17][C@H:16]2[C@@:11]3([CH3:35])[CH2:12][CH2:13][C@@:14]3([C@H:31]([OH:34])[CH2:32][NH:33][CH2:57][C:56]4[CH:59]=[CH:60][C:53]([Cl:52])=[CH:54][CH:55]=4)[CH2:26][C:25](=[O:27])[C:24]([CH:28]([CH3:30])[CH3:29])=[C:15]32)[C:6]1([CH3:37])[CH3:38])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 77264-ChlorobenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydride2×HCID 86690407HCID 86690407, compound

Product 1

HCID 86690406HCID 86690406, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a flask containing (3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((S)-2-amino-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl acetate (200 mg, 379 mmol) and methanol (15 ml) was added triethylamine (15 mg, 0.152 mmol), magnesium sulfate (68 mg, 0.168 mmol) and 4-chlorobenzaldehyde (64 mg, 0.455 mmol). The contents were allowed to stir at ambient temperature for approximately 2 hours. To the resulting mixture was added sodium borohydride (17 mg, 455 mmol) in a single portion and the reaction was allowed to stir at ambient temperature for two and a half days. The reaction was then charged with an additional 20% excess of the p-Cl-benzaldehyde and sodium borohydride and allowed to stir an additional 2 hours. Finally, the reaction was quenched with water, allowed to stir 15 minutes and solids filtered to provide title compound contaminated with impurities. LC/MS: m/z calculated 651.4. found 652 (M+1)+.

Workup

  1. stirringto stir at ambient temperature for two and a half days
  2. stirringto stir an additional 2 hours
  3. customFinally, the reaction was quenched with water
  4. stirringto stir 15 minutes
  5. filtrationsolids filtered

Sources & evidence

ORD record
ord-1dc31060b79d4ccbabf9ba01d7c8a21f
Source dataset
uspto-grants-2015_08
Patent number
US09102685B2

Reaction notes

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