Ammonium formate → HCID 11123158, compound

HRID 2372553Notes

Reaction equation

HRID 2372553 reaction equation
[C:1]([O:4][C@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:7]([C@H:8]([N+:32]([O-])=O)[CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6]1)(=[O:3])[CH3:2].C([O-])=O.[NH4+]>C1COCC1.CO.[Pd].CCOCC>[C:1]([O:4][C@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:7]([C@H:8]([NH2:32])[CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 10961777HCID 10961777, compound

Product 1

HCID 11123158HCID 11123158, compoundYield 82.1%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3β-acetoxy-6β-nitro-5α-cholestane (0.474 g, 0.001 mole) in THF (5 mL) and methanol (5 mL) was added 10% palladium on carbon (50 mg) followed by ammonium formate (0.315 g, 5 equivalents). The resulting mixture was stirred at room temperature for 50 minutes then diluted with Et2O, filtered and evaporated in vacuo. Flash column chromatography (SiO2, 4:1, hexane:Et2O) gave 3β-acetoxy-6β-amino-5α-cholestane (0.366 g, 82%).

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-ae414aa859974b5dbacec7968a6ae51f
Source dataset
uspto-grants-1992_03
Patent number
US05099067

Reaction notes

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