1-Bromoadamantane → Adamantane

HRID 1955961Notes

Reaction equation

HRID 1955961 reaction equation
[C:1]12(Br)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[SnH4]>>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

3

Reactant 2

HCID 791061-BromoadamantaneHCID 123161Stannane

Product 1

HCID 9238AdamantaneYield 90%

Procedure

Adamantyl bromide was cleanly reduced over approximately 3 hours with 1.2 equiv of fluorous tin hydride reagent 3 in refluxing BTF (stoichiometric procedure). After evaporation of the BTF and liquid-liquid extraction (PFMC-CH2Cl2) to separate the tin products, adamantane was isolated in 90% yield (as determined by GC integration). Under the stoichiometric procedure, fluorous tin hydride reagent 3 reduces a number of other functional groups besides halides, as shown in FIG. 1. In these substrates, the nitro, phenylseleno, or xanthate groups are replaced by hydrogen.

Workup

  1. temperaturein refluxing BTF (stoichiometric procedure)
  2. customAfter evaporation of the BTF and liquid-liquid extraction (PFMC-CH2Cl2)
  3. customto separate the tin products

Sources & evidence

ORD record
ord-6c505ceba46d4ec68f0abdfa6fbfa533
Source dataset
uspto-grants-1998_07
Patent number
US05777121

Reaction notes

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